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281-23-2 Usage

Chemical Description

Adamantane is a hydrophobic portion of the molecule connected to variously substituted aryl groups through the cyanoguanidine linker.

Discovery History

In 1932, Landa et al (Czech) has discovered adamantane from the petroleum fractions in the oilfield of the South Moravia. In the following year, he has applied X-ray technology for confirming its structure. Adamantane was first successfully synthesized by the chemist Vladimir Prelog (Yugoslavia) during the period of living in Switzerland in 1941. At that time, it was synthesized through stepwise synthesis method via twenties steps. Adamantane was a fairly expensive compound at that time. In 1957, when chemist Paul Schleyer from Princeton chemist tried to use aluminum chloride as a catalyst for heating endo-type hydrogenated dicyclopentadiene and transform it into exo isomer, he unexpectedly found that the reaction product contains approximately 10% of adamantane as the byproduct. Paul Schleyer grasped this opportunity and increased the yield of adamantane through optimizing the conditions for increasing the yield of adamantane. Therefore, people can obtain adamantane from the cheap petrochemical products: cyclopentadiene dimer through a simple two steps reaction. Since then, the price of adamantane, like an avalanche fell down, became a very cheap and easily available compound. Because of that the special cage structure of adamantane has caused great interest to the chemical community, this gave birth to the field of the caged compound chemistry. Later it was found that amantadine has antiviral activity, this had further attracted special attention from the medicine community. Now in the chemical community, the systematic research has around adamantane has already formed an independent discipline: adamantane chemistry. 1-Adamantyl group is bulky and stable substituent presented in some Persistent carbene. The famous Jacobson Asymmetric Diels-Alder reaction catalyst also contains an adamantly group.

Clustered compound

Adamantane is a tricyclic aliphatic hydrocarbon, belonging to cluster-like compound and is naturally presented in the petroleum with the content being about four millionths. It is obtained through the reaction between dicyclopentadiene and hydrogen in the nickel catalyst and aluminum trichloride catalyst. It is a cyclic tetrahedral configuration containing 10 carbon atoms, 16 hydrogen atoms, forming a high symmetry cage-like compound. Because of its spatial arrangement of carbon atoms is generally the same as the basic unit of the diamond lattice, it gets its derived reputation name adamantane. Adamantane is characterized by high thermal stability, excellent lubricity, great pro-oil capacity and no taste as well as lower reactivity than benzene. The hydrogen in the bridgehead carbon atoms (1, 3, 5, 7) has high chemical activity and can have substitution reaction to generate many derivatives: 1-bromo-adamantane, 1-nitro-adamantane, 1-amino-adamantane hydrochloride and 1-adamantyl ethylamine hydrochloride (it can prevent the influenza caused by the A2 virus) and so on; it can also be oxidized to form diamond alcohol and can also be used to make specialty polymers, in particular optical and photosensitive material; it can also be used for gasoline production as well as the production of co-catalysts, lubricants and drugs. Moreover, it can also be used as agricultural chemicals and daily used chemicals and so on and is a good and novel organic material. The above information is edited by the lookchem of Dai Xiongfeng.

Amantadine

Amantadine, after entering into the brain tissue can promote the release of dopamine, or delay the metabolism of dopamine to play anti-parkinsonian effect and is anti-Parkinson drugs. Meanwhile, the mechanism of anti-Parkinson's disease is through promoting the synthesis and release of dopamine in the striatum and reducing the reuptake of neurons on dopamine together with anti-acetylcholine effect, thereby alleviating the symptoms of Parkinson's disease with excellent effect on the limb rigidity. Its effect is maintained generally not more than one year. Long-term application of such drugs is not recommended since it can have side effects on the cardiovascular. Amantadine is the earliest antiviral agent for inhibiting influenza virus. The United States had ratified it as a preventive medicine during the flu epidemic in 1966 and had further confirmed it as a therapeutic agent on the basis of being as preventive drug in 1976. The efficacy and safety for this drug on the adult patients has been widely recognized. But the treatment dose and the dose for causing side effects are very close to each other. Moreover, the dosage and dosing schedules for the elderly and patients of chronic heart and lung disease or kidney disease is very difficult to determine, and therefore not yet widely accepted in clinical application. In Japan, amantadine has been always used as the therapeutic agent for Parkinson's disease and was only approved for the treatment of influenza A virus infection diseases until 1998. Indications It has significant efficacy in treating Tremor paralysis with good efficacy in alleviating tremor and rigidity with rapid onset. It exerts obvious effect at 48 hours after the treatment and the effect will reach peak after two weeks. The drug is subject to renal excretion in its prototype with the acidic urine being able to accelerate the excretion rate. Asian A-II anti-influenza virus effect has an about 70% protection rate when being in contact with patients of this type of flu. Its antipyretic effect is effective on a variety of inflammation, sepsis and viral pneumonia, when combined with antibiotics, the antipyretic effect is better than single administration of antibiotics.

Chemical Properties

It appears as colorless crystals.

Uses

Different sources of media describe the Uses of 281-23-2 differently. You can refer to the following data:
1. Adamantane is a tetrahedral cyclic hydrocarbon containing 10 carbon atoms and 16 hydrogen atoms with its basic structure being the chair form of cyclohexane. It is a highly symmetric and very stable compound. Adamantane has the following characteristics: (1) very stable to light (2) good lubrication force; (3) highly lipophilic: (4) almost tasteless and is sublimate; (5) Although the reactivity is not as active as the reactivity of benzene, but synthesizing of its derivatives is very easy. It is mainly used for the synthesis of special drugs of anti-cancer and anti-tumor. It can also be used to prepare advanced lubricants, the surfactants of photosensitive material, pesticides, catalysts and the like. The hydrogen atom of its bridgehead carbon atoms (i. e. 1, 3, 5, and 7) is easy to have substitution reaction. E.g. adamantane has reaction with an excess amount of bromine, generating 1-bromo-adamantane; reaction with nitrogen dioxide at 175 °C can yield 1-Polynitroadamantanes; oxidation between chromium trioxide and acetic acid can form a 1-adamantyl alcohol. Adamantane can also be obtained through the isomerization between tetrahydro-dicyclopentadiene in the presence of anhydrous aluminum chloride. Its derivative can be used as medicaments, e.g., 1-amino-adamantane hydrochloride and 1-adamantyl triethylamine hydrochloride can prevent the influenza caused by the virus A2. Adamantane can be used for the synthesis of adamantane derivative. It can often be used as pharmaceutical intermediates as well as being used as the raw material of light-sensitive material, cosmetic and surfactant intermediates and also the epoxy curing agent.
2. synthon for Amantadine, Rimantadine, Somantadine, Tromantadine
3. The diamine as curing agent for epoxy resins [US 3053907 (1962 to du Pont)].
4. Adamantane is mainly used for the synthesis of medicine to treat influenza, serve as NMDA receptor channel blockers. Also be used for preparation of advanced lubricants, photographic material, surface active agents, catalysts and other products.

Production method

Adamantane is presented in the petroleum with the content being about four millionths. Adamantane can be obtained through via the catalyzed hydrogenation of dicyclopentadiene into tetrahydro-dicyclopentadiene and further isomerization in the presence of anhydrous aluminum chloride. The technical process is as follows: 1. catalytic hydrogenation; put the dicyclopentadiene and nickel catalyst into the autoclave, use nitrogen to displace the air in the autoclave. Then start the mixing hydrogen reaction. The pressure during the first half stage should be 0.5-0.7MPa while the latter stages pressure should be 1.5-2MPa with the temperature being 120 ℃ and continued for about 12h until no hydrogen absorption occurs any more. Stand for 3-4h and have stratification, apply sampling tests and the olefin content should be less than 2%. 2. Isomerization; add the Tetrahydro-dicyclopentadiene to a dry glass-lined tank, then add anhydrous aluminum chloride, heat at 35°C, stir and dissolve. Add drop wise of water within 3 h and gradually raise the temperature to 75 °C with being cooled to 40 °C after 5 h of reaction. Add water to destroy the aluminum trichloride and start steam distillation, collect the distilled adamantane, drain and wash with a small amount of acetone to give adamantane.

Definition

adamantane: A colourless crystallinehydrocarbon C10H16; m.p.269°C. It is found in certain petroleumfractions. The structure containsthree symmetrically fusedcyclohexane rings.

Synthesis Reference(s)

Journal of the American Chemical Society, 91, p. 6779, 1969 DOI: 10.1021/ja01052a041The Journal of Organic Chemistry, 51, p. 3038, 1986 DOI: 10.1021/jo00365a034

Purification Methods

Crystallise adamantane from acetone or cyclohexane, and sublime it in a vacuum below its melting point [Butler et al. J Chem Soc, Faraday Trans I 82 535 1986]. Adamantane is also purified by dissolving it in n-heptane (ca 10mL/g of adamantane) on a hot plate, adding activated charcoal (2g/100g of adamantane), and boiling for 30minutes, filtering the hot solution through a filter paper, concentrating the filtrate until crystallisation just starts, adding one quarter of the original volume of n-heptane, and allowing to cool slowly over a period of hours. The supernatant is decanted off and the crystals are dried in vacuo at 25o. [Prelog & Seiwerth Chem Ber 74 1769 1941, Schleyer et al. Org Synth Coll Vol V 16 1973, Walter et al. J Am Chem Soc 107 793 1985.] [Beilstein 5 III 393, 5 IV 469.]

Check Digit Verification of cas no

The CAS Registry Mumber 281-23-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,8 and 1 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 281-23:
(5*2)+(4*8)+(3*1)+(2*2)+(1*3)=52
52 % 10 = 2
So 281-23-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H16/c1-7-2-9-4-8(1)5-10(3-7)6-9/h7-10H,1-6H2/t7-,8+,9-,10+

281-23-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A14041)  Adamantane, 98%   

  • 281-23-2

  • 50g

  • 477.0CNY

  • Detail
  • Alfa Aesar

  • (A14041)  Adamantane, 98%   

  • 281-23-2

  • 250g

  • 1272.0CNY

  • Detail
  • Alfa Aesar

  • (A14041)  Adamantane, 98%   

  • 281-23-2

  • 1000g

  • 4058.0CNY

  • Detail
  • Aldrich

  • (100277)  Adamantane  ≥99%

  • 281-23-2

  • 100277-25G

  • 400.14CNY

  • Detail
  • Aldrich

  • (100277)  Adamantane  ≥99%

  • 281-23-2

  • 100277-100G

  • 1,133.73CNY

  • Detail

281-23-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name adamantane

1.2 Other means of identification

Product number -
Other names Adamantane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:281-23-2 SDS

281-23-2Synthetic route

1-Adamantyl bromide
768-90-1

1-Adamantyl bromide

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With triethylsilane; dilauryl peroxide; 1-dodecylthiol at 70℃; for 1h;100%
With triethylsilane; dilauryl peroxide; 1-dodecylthiol In cyclohexane at 80℃; for 1h;100%
With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); cPS-SnBu2Cl In 1,2-dimethoxyethane at 80℃; for 0.5h;100%
1-adamantyl isocyanide
22110-53-8

1-adamantyl isocyanide

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With Perbenzoic acid; diphenylsilane In 1,4-dioxane for 1h; Heating;100%
1-(phenylseleno)tricyclo<3.3.1.13,7>decane
75480-69-2

1-(phenylseleno)tricyclo<3.3.1.13,7>decane

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); 1,1,2,2-tetraphenyldisilane In ethyl acetate for 14h; Reduction; Heating;100%
With Perbenzoic acid; methyl phosphite In 1,4-dioxane for 5h; Heating;41 % Chromat.
O-(adamantan-1-yl) S-methyl carbonodithioate
79057-62-8

O-(adamantan-1-yl) S-methyl carbonodithioate

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With sodium formate; (Bu4N)2S2O8 In N,N-dimethyl-formamide at 75℃; for 0.5h; Barton-McCombie deoxygenation;100%
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 130℃; for 0.0833333h; Barton-McCombie deoxygenation;77%
With 1-ethyl-piperidine; 2,2'-azobis(isobutyronitrile); hypophosphorous acid In 1,4-dioxane for 1h;100 % Chromat.
With dibutylphosphine oxide; 1,1'-azobis(1-cyanocyclohexanenitrile) In 1,4-dioxane for 8h; Heating;90 % Chromat.
1-adamanthanol
768-95-6

1-adamanthanol

A

adamantane
281-23-2

adamantane

B

2-(1-adamantyl)propane
773-32-0

2-(1-adamantyl)propane

Conditions
ConditionsYield
With triisopropylborane; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane 1.) -30 deg C, 30 min 2.) room temp., 6 h;A 99.9%
B 0.1%
1-adamanthanol
768-95-6

1-adamanthanol

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With hydrogen; aluminum oxide; nickel at 180℃;99%
With indium(III) chloride; diphenylsilyl chloride In 1,2-dichloro-ethane at 80℃; for 3h;99%
With boron trifluoride diethyl etherate In water for 2h; Inert atmosphere; Reflux;29%
1-adamantanol
700-57-2

1-adamantanol

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With hydrogen; aluminum oxide; nickel at 170℃;99%
Multi-step reaction with 2 steps
1: 81 percent / NaI; HI / 48 h / 90 - 100 °C
2: 35 percent Chromat. / t-BuOK / dimethylsulfoxide / 3 h / Irradiation
View Scheme
Multi-step reaction with 2 steps
1: 81 percent / NaI; HI / 48 h / 90 - 100 °C
2: 20 percent Chromat. / t-BuOK / dimethylsulfoxide / 3 h / Irradiation
View Scheme
(3aR,4R,7S,7aS)-octahydro-1H-4,7-methanoindene
2825-83-4

(3aR,4R,7S,7aS)-octahydro-1H-4,7-methanoindene

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With tris(trifluoromethanesulfonyloxy)boron In 1,1,2-Trichloro-1,2,2-trifluoroethane at 0 - 20℃; for 0.5h;98%
With tris(trifluoromethanesulfonyloxy)boron In 1,1,2-Trichloro-1,2,2-trifluoroethane at 0 - 20℃; for 0.5h; Product distribution; sonication, other C(4n+6)H(4n+12), (n=1-3), other polycyclic hydrocarbon, other reactants, reaction condition;98%
With aluminium trichloride at 150 - 180℃;
Mechanism; application of the "prinzip of minimal chemical distance";
1-iodoadamantane
768-93-4

1-iodoadamantane

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); (C6F13CH2CH2)3SnH; sodium cyanoborohydride In tert-butyl alcohol at 90℃; for 3h;98%
With air; tributyl borane; water In benzene at 20℃;97%
With 1,3-bis(2,6-diiopropylphenyl)imidazol-2-ylidene borane In 1,2,3-trifluorobenzene at 140℃; for 12h;97%
1-iodoadamantane
768-93-4

1-iodoadamantane

A

adamantane
281-23-2

adamantane

B

1-adamantanol

1-adamantanol

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tributyltin chloride; sodium cyanoborohydride; oxygen-18 In tert-butyl alcohol at 60℃; for 16h; Yields of byproduct given;A n/a
B 98%
2-methyladamantane
700-56-1

2-methyladamantane

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With hydrogen; aluminum oxide; nickel at 235℃; under 760 Torr; for 4h;97%
Octahydro-1,2,4-metheno-1H-cyclobutapentalene
6707-86-4, 62928-75-0

Octahydro-1,2,4-metheno-1H-cyclobutapentalene

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With sodium tetrahydroborate; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane at -78 - 20℃; for 18h;97%
1-acetyloxyadamantane
22635-62-7

1-acetyloxyadamantane

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With hafnium(IV) trifluoromethanesulfonate; palladium 10% on activated carbon; hydrogen In neat (no solvent) at 125℃; under 750.075 Torr; for 18h; Time;97%
With di-tert-butyl peroxide; (4-diphenylsilylphenyl)diphenylsilane at 140℃; for 15h;85%
N-(adamantan-1-yl)-N-methylacetamide
3717-37-1

N-(adamantan-1-yl)-N-methylacetamide

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With sulfuric acid In ethanol; water for 44h; Heating;97%
2-Adamantanone
700-58-3

2-Adamantanone

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With triethylsilane; 2C2H3F3O*BF3 In dichloromethane at 20℃; for 3h;97%
With gallium(III) triflate; dimethylmonochlorosilane In dichloromethane at 20℃; for 0.5h;88%
With triethylsilane; 2C24BF20(1-)*C21H16N3P(2+) In dichloromethane at 120℃; for 13h; Inert atmosphere;94 %Spectr.
1-Adamantyl bromide
768-90-1

1-Adamantyl bromide

trimethylstannane
1631-73-8

trimethylstannane

A

adamantane
281-23-2

adamantane

B

n-butyltrimethyltin
1527-99-7

n-butyltrimethyltin

Conditions
ConditionsYield
With n-butyllithium In hexane 1-bromoadamantane (1 equiv.) and TMTH (1 equiv.) in hexane cooled to 0°C under Ar, n-BuLi (1 equiv., 2.40 M in hexane) added, stirred for 15 min, quenched with water; analyzed by GC;A 97%
B 95%
1-adamantanemethanol
770-71-8

1-adamantanemethanol

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With hydrogen; aluminum oxide; nickel at 200℃;96%
With cerium(III) chloride; 9,10-diphenylanthracene; 1,2-bis(2,4,6-triisopropylphenyl)disulfane; tetrabutyl-ammonium chloride In acetonitrile for 24h; Irradiation; Inert atmosphere;95%
bi(cyclopentadiene)
77-73-6, 933-60-8, 1755-01-7

bi(cyclopentadiene)

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With sodium tetrahydroborate; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane at -78 - 20℃; for 18h;96%
With sodium tetrahydroborate; trifluoric acid In 1,1,2-Trichloro-1,2,2-trifluoroethane at -78 - 20℃; for 18h; Product distribution; other unsaturated polycyclics;96%
1-(adamantane-1-carbonyloxy)pyridine-2(1H)-thione
91233-19-1

1-(adamantane-1-carbonyloxy)pyridine-2(1H)-thione

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With 9-borabicyclo[3.3.1]nonane dimer; tri-n-butyl-tin hydride In toluene at 0℃;96%
With thiophenol In tetrahydrofuran at -80℃; Product distribution; Mechanism; Irradiation;
With 2,2'-azobis(isobutyronitrile); Tris(trimethylsilyl)methane In benzene at 80℃;89 % Chromat.
1-iodoadamantane
768-93-4

1-iodoadamantane

A

adamantane
281-23-2

adamantane

B

1-adamanthanol
768-95-6

1-adamanthanol

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); oxygen; tert-butyldibutyltin chloride; sodium cyanoborohydride In tert-butyl alcohol at 60℃; for 20h; Yields of byproduct given;A n/a
B 96%
With 2-(2-methoxyethoxy)ethyl alcohol; oxygen; sodium hydride In 1,4-dioxane at 20℃; for 24h; Schlenk technique; chemoselective reaction;A 42%
B n/a
2-adamantyl bromide
7314-85-4

2-adamantyl bromide

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With [2-(di-tert-butylphosphinomethyl)-6-(diethylaminomethyl)pyridine]ruthenium(II) chlorocarbonyl hydride; isopropyl alcohol; sodium t-butanolate at 100℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;95%
With air; diethylzinc; tri-n-butyl-tin hydride In benzene at 20℃; for 1h;90%
With water; zinc In acetonitrile at 80℃; for 41h; Inert atmosphere; Sealed tube;53%
octahydro-4,7-methano-inden-5-one
13380-94-4

octahydro-4,7-methano-inden-5-one

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With sodium tetrahydroborate; trifluorormethanesulfonic acid In 1,1,2-Trichloro-1,2,2-trifluoroethane at -78 - 20℃; for 18h;95%
1-Adamantanecarboxylic acid
828-51-3

1-Adamantanecarboxylic acid

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With hydrogen; aluminum oxide; nickel at 180℃; Pd/SiO2, 330 deg C;95%
Multi-step reaction with 2 steps
1: DCC, DMAP
2: 93 percent / Bu3SnH, AIBN / benzene / 3 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 28 percent / 85percent H2O2
2: 3 percent Chromat. / cyclohexane / 81 °C
View Scheme
1,3-dichloroadamantane
16104-50-0

1,3-dichloroadamantane

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium; N,N-diethyl-1,1,1-trimethylsilanamine In diethyl ether for 6h; Ambient temperature;95%
1-iodoadamantane
768-93-4

1-iodoadamantane

4-Cyano-benzenethiolatetetramethyl-ammonium;

4-Cyano-benzenethiolatetetramethyl-ammonium;

A

adamantane
281-23-2

adamantane

B

bis(4-cyanophenyl)disulfane
6339-51-1

bis(4-cyanophenyl)disulfane

C

4-(adamantan-1-ylthio)benzonitrile

4-(adamantan-1-ylthio)benzonitrile

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; Irradiation;A 3%
B n/a
C 95%
C24H25NO2Se
195874-42-1

C24H25NO2Se

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 3h; Heating;93%
adamantane-1-carboxylate
36712-30-8

adamantane-1-carboxylate

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With triethylsilane; C19H3BF14 In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;93%
ethyl dispiro[1,3-dithiolane-2',2;4',2''-bis(adamantane)]-5'-carboxylate
98922-03-3

ethyl dispiro[1,3-dithiolane-2',2;4',2''-bis(adamantane)]-5'-carboxylate

A

adamantane
281-23-2

adamantane

B

(2-Adamantyl)essigsaeure-ethylester
59210-87-6

(2-Adamantyl)essigsaeure-ethylester

Conditions
ConditionsYield
nickel In methanolA n/a
B 92%
1-chloroadamantane
935-56-8

1-chloroadamantane

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With zirconocene dichloride; triethyl borane In tetrahydrofuran; hexane at 25℃; for 5h;92%
With iron(III) chloride; phenylsilane; sodium methylate In tetrahydrofuran for 12h; Schlenk technique; Inert atmosphere;89%
With Schwartz's reagent; triethyl borane In tetrahydrofuran at 25℃; for 17h;88%
1-Adamantyl bromide
768-90-1

1-Adamantyl bromide

bromotris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)stannane

bromotris(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)stannane

adamantane
281-23-2

adamantane

Conditions
ConditionsYield
With azobisisobutyronitrile; sodium cyanoborohydride In α,α,α-trifluorotoluene; tert-butyl alcohol92%
With azobisisobutyronitrile; sodium cyanoborohydride In α,α,α-trifluorotoluene; tert-butyl alcohol92%
C6(C6H4CH3)3(C6H4C5H4N)3

C6(C6H4CH3)3(C6H4C5H4N)3

adamantane
281-23-2

adamantane

C10H16*4C60H45N3

C10H16*4C60H45N3

Conditions
ConditionsYield
In water-d2; d(4)-methanol at 19.84℃; for 0.0833333h;100%
adamantane
281-23-2

adamantane

A

1-Adamantyl bromide
768-90-1

1-Adamantyl bromide

B

1,3-dibromoadamantane
876-53-9

1,3-dibromoadamantane

Conditions
ConditionsYield
With iron(III)-acetylacetonate; carbon tetrabromide Reagent/catalyst; Sealed tube; Inert atmosphere;A 99%
B 23%
With bromine; iron at 0 - 50℃; for 3h;A n/a
B 93%
With iodine(I) bromide In tetrachloromethane for 3h; Heating;A 75 % Chromat.
B 25 % Chromat.
With iodine(I) bromide In tetrachloromethane for 3h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
adamantane
281-23-2

adamantane

1-adamanthanol
768-95-6

1-adamanthanol

Conditions
ConditionsYield
With Fe(AAEMA)3; oxygen; isovaleraldehyde In 1,2-dichloro-ethane under 760 Torr; for 60h; Ambient temperature;99%
With oxone; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate In dichloromethane; water at 0 - 25℃; under 3878.71 Torr; for 0.0222222h; Reagent/catalyst; Temperature; Solvent;99%
With water; bromine for 1h; Ambient temperature;95%
adamantane
281-23-2

adamantane

1-(1-adamantyl)chlorophosphinoyladamantane
126683-99-6

1-(1-adamantyl)chlorophosphinoyladamantane

Conditions
ConditionsYield
With aluminum (III) chloride; phosphorus trichloride for 6.16667h; Reflux;99%
Stage #1: adamantane With aluminum (III) chloride; phosphorus trichloride Reflux;
Stage #2: With water Cooling with ice;
99%
With aluminium trichloride; phosphorus trichloride for 5h; Heating;95%
With aluminium trichloride; phosphorus trichloride for 5h; Heating;86.2%
With aluminium trichloride; water; phosphorus trichloride 1.) reflux, 6 h, 2.) chloroform; Yield given. Multistep reaction;
adamantane
281-23-2

adamantane

adamantane-d16
30470-60-1

adamantane-d16

Conditions
ConditionsYield
With d8-isopropanol; 5% rhodium-on-charcoal; 10% Pt/activated carbon; water-d2 at 120℃; for 24h; Sealed tube;99%
adamantane
281-23-2

adamantane

1-Adamantyl bromide
768-90-1

1-Adamantyl bromide

Conditions
ConditionsYield
With bromine; Nitrogen dioxide In trifluoroacetic acid at 20℃; for 0.5h;98%
With water; bromine for 0.166667h;93%
With bromine at 85 - 110℃; Temperature;93%
adamantane
281-23-2

adamantane

1,3-dichloroadamantane
16104-50-0

1,3-dichloroadamantane

Conditions
ConditionsYield
With Iodine monochloride In tetrachloromethane for 5h; Heating;98%
With chlorosulfonic acid at 0 - 25℃; for 10h;98%
With chlorosulfonic acid at 0 - 25℃; for 8h;98%
adamantane
281-23-2

adamantane

2-Adamantanone
700-58-3

2-Adamantanone

Conditions
ConditionsYield
With oxone; 1,1,1-trifluoro-2-propanone; sodium hydrogencarbonate In dichloromethane; water at 0 - 25℃; under 3878.71 Torr; for 0.0222222h;98%
With potassium sulfate; sulfuric acid at 40 - 55℃; for 40h; Product distribution / selectivity;87%
With lithium sulfate; sulfuric acid at 40 - 55℃; for 40h; Product distribution / selectivity;87%
adamantane
281-23-2

adamantane

1-chloroadamantane
935-56-8

1-chloroadamantane

Conditions
ConditionsYield
With tetrachloromethane; manganese(III) acetylacetonate; acetonitrile at 200℃; for 1h;98%
With Iodine monochloride In tetrachloromethane for 0.25h; Ambient temperature;97%
With tetrachloromethane; ferrocene; ethanol at 160℃; for 6h; Sealed tube;93%
adamantane
281-23-2

adamantane

A

1-chloroadamantane
935-56-8

1-chloroadamantane

B

1,3-dichloroadamantane
16104-50-0

1,3-dichloroadamantane

Conditions
ConditionsYield
With tetrachloromethane; K10 bentonite; iron(III) chloride for 40h; Heating;A 2%
B 98%
With tetrachloromethane; bis(acetylacetonate)oxovanadium; water at 160℃; for 6h; Sealed tube;A 90%
B n/a
With thionyl chloride; n-Butyl chloride; sulfuric acid at 30℃; for 30h;A 73%
B 10.5%
adamantane
281-23-2

adamantane

1,3,5,7-tetrachloroadamanatane
21336-43-6

1,3,5,7-tetrachloroadamanatane

Conditions
ConditionsYield
With tetrachloromethane; aluminium trichloride for 1h; Heating;98%
With aluminum (III) chloride In tetrachloromethane Reflux;91%
tertiary butyl chloride
507-20-0

tertiary butyl chloride

adamantane
281-23-2

adamantane

1-tert-butyladamantane
20440-81-7

1-tert-butyladamantane

Conditions
ConditionsYield
With Rh(PPh3)3Cl In dichloromethane at 150℃; for 3h;98%
adamantane
281-23-2

adamantane

1,3-dibromoadamantane
876-53-9

1,3-dibromoadamantane

Conditions
ConditionsYield
With bromine; iron In 1,1,2-Trichloro-1,2,2-trifluoroethane at 30℃; for 8h;97.3%
With bromine; iron at 20℃; for 2h; Cooling with ice;96%
With bromine at 0 - 25℃;85%
adamantane
281-23-2

adamantane

acetonitrile
75-05-8

acetonitrile

N-(1-adamantyl)acetamide
880-52-4

N-(1-adamantyl)acetamide

Conditions
ConditionsYield
With nitrosonium tetrafluoroborate for 4h; reflux;97%
With sulfuric acid at 3 - 25℃; for 5h;97%
With bromine for 0.666667h; Ambient temperature;96%
adamantane
281-23-2

adamantane

A

2-Adamantanone
700-58-3

2-Adamantanone

B

1-adamanthanol
768-95-6

1-adamanthanol

C

1-adamantanol
700-57-2

1-adamantanol

Conditions
ConditionsYield
With [2,2]bipyridinyl; Ba; trifluoroacetic acid In dichloromethane at 20℃; for 0.0333333h; Product distribution;A n/a
B 97%
C n/a
With [2,2]bipyridinyl; Ba; trifluoroacetic acid In dichloromethane at 20℃; for 0.0333333h; Yields of byproduct given;A n/a
B 97%
C n/a
With ammonium cerium(IV) nitrate; oxygen In acetonitrile for 5h; Ambient temperature; Irradiation;A 5%
B 85%
C 5%

281-23-2Relevant articles and documents

Reactions of 2-Iodo- and 1,2-Dihaloadamantanes with Carbanions in DMSO by the SRN1 Mechanism

Lukach, Andres E.,Rossi, Roberto A.

, p. 5826 - 5831 (1999)

The reaction of 2-iodoadamantane (1) with the potassium enolate of acetophenone (2) did not occur in the dark but succeeded under irradiation or in the presence of FeBr2 to give the substitution product 3 in 62% and 88% yields, respectively. The photostimulated reaction was inhibited by p-dinitrobenzene (p-DNB). There was no reaction of 1 with the anion of nitromethane (4) in the dark or under irradiation. However, 4 reacted with 1 in the presence of acetone enolate ion (entrainment reaction) to yield 88% of the substitution product 2-adamantylnitromethane (5). The photostimulated reaction of 1 with anthrone (6), 2-naphthyl methyl ketone (9), and N-acetylthiomorpholine (11) anions afforded the substitution compounds 7 (37%), 10 (32%), and 12 (20%), respectively. There was no reaction of 1-chloro-2-iodoadamantane (13) with 2 in the dark (2 h), but under irradiation (5 min) it yielded 52% of the monosubstitution product α-(1-chloro-2-adamantyl)-acetophenone (14). Under longer irradiation time (3 h), the same yield of 14 (52%) was obtained but the disubstitution product 15 was formed in 45% yield. Product 15 was also formed in the photostimulated reaction of 14 with 2. 2-Chloro-1-iodoadamantane (18) did not react with 2 in the dark (2 h), but the photostimulated reaction yielded the monosubstitution product α-(2-chloro-1-adamantyl)acetophenone (19) in 53% and 15 in 4% yield. Products 14 and 19 are intermediates in the formation of 15 in these reactions. There was a slow dark reaction of 1,2-diiodoadamantane (20) with 4 in the presence of acetone enolate ion to afford the iodomonosubstitution compound 21 (40%) and the disubstitution product 22 (13%). The photostimulated reaction (25 min) gave 21 (48%) and 22 (41%). On the other hand, after 3 h of irradiation, only traces of 21 could be detected (5%) and the product distribution consisted mainly of 22. The iodomonosubstitution product 21 is an intermediate in these reactions.

RITTER REACTIONS. II. REDUCTIVE DEAMIDATION OF N-BRIDGEHEAD AMIDES

Bishop, Roger,Burgess, Graham

, p. 1585 - 1588 (1987)

Adamantyl- or homoadamantyl-derived N-bridgehead amides are converted in high yields into hydrocarbon derivatives on prolonged reflux in ethanol and 50percent sulphuric acid (1:1 by volume).This process probably involves AAL1 hydrolysis to the tertiary carbonium ion, followed by hydride abstraction from the ethanol solvent.

Development of a new ultraporous polymer as support in organic synthesis.

Deleuze, Herve,Maillard, Bernard,Mondain-Monval, Olivier

, p. 1877 - 1880 (2002)

This paper describes the preparation and post-functionalisation of a new polymeric support based on emulsion-derived foams and called polyHIPEs. The remaining pendant vinylic bonds are easily functionalised by a free radical mechanism. The large pores and channels of this material allow an easy access of the reagent in solution toward the grafted species. PolyHIPE-supported thiol, in the presence of an excess of triethylsilane, showed a good activity and selectivity toward reductive cyclisation of 6-bromohex-1-ene and 1-allyloxy-2-bromobenzene.

Smith,Billups

, p. 4307,4310 (1974)

-

Schleyer

, p. 3292 (1957)

-

Regiochemistry of the photostimulated reaction of the phthalimide anion with 1-iodoadamantane and tert-butylmercury chloride by the SRN1 mechanism

Maquieira, Manuel Bajo,Penenory, Alicia B.,Rossi, Roberto A.

, p. 1012 - 1015 (2002)

The photostimulated reaction of the phthalimide anion (1) with 1-iodoadamantane (2) gave 3-(1-adamantyl) phthalimide (3) (12%) and 4-(1-adamantyl) phthalimide (4) (45%), together with the reduction product adamantane (AdH) (21%). The lack of reaction in the dark and inhibition of the photoinduced reaction by p-dinitrobenzene, 1,4-cyclohexadiene, and di-tert-butylnitroxide indicated that 1 reacts with 2 by an SRN1 mechanism. Formation of products 3 and 4 occurs with distonic radical anions as intermediates. The photoinduced reaction of anion 1 with tert-butylmercury chloride (10) affords 4-tert-butylphthalimide (11) as a unique product. By competition experiments toward 1, 1-iodoadamantane was found to be ca. 10 times more reactive than tert-butylmercury chloride.

Hypophosphorous acid and its salts: New reagents for radical chain deoxygenation, dehalogenation and deamination

Barton,Jang,Jaszberenyi

, p. 5709 - 5712 (1992)

Thionocarbonates and xanthates of alcohols, bromides, iodides and isonitriles can be transformed to the corresponding hydrocarbons with hypophosphorous acid or its salts in radical chain reactions.

Reductive dehalogenation of 1,3-dibromoadamantane by sodium methoxide in methanol

Skomorokhov, M.Yu.,Klimochkin, Yu.N.

, p. 1913 - 1914 (2011)

-

Carbene rearrangements, 60. Supramolecular structure-reactivity relationships: Photolysis of a series of aziadamantane@cyclodextrin inclusion complexes in the solid state

Krois, Daniel,Brecker, Lothar,Werner, Andreas,Brinker, Udo H.

, p. 1367 - 1374 (2004)

Photolyses of the α-, β- and γ-cyclodextrin complexes of 2-aziadamantane (1) in the solid state afforded markedly different product distributions, as determined by quantitative GC and HPLC analyses. The results are discussed with respect to the structures of the inclusion complexes.

Synthesen von Tricyclo4,8>decan (2-Homobrendan)

Jaeggi, Franz Josef von,Buchs, Peter,Ganter, Camille

, p. 872 - 886 (1980)

Three different approaches to tricyclo4,8>decane (5) (and derivatives thereof), one of the 19 isomeric hydrocarbons of the 'adamantaneland', are described: 1) Cyclization of properly functionalized bicyclooctanes as 32 (cyclialkylation), 40 + 42 (thermocyclization) and 44 + 45 (photocyclization); 2) Silver(I)-ion catalyzed rearrangement of 5,7- and 5,10-Dehydroprotoadamantane (63 and 64, respectively) yielding tricyclo4,8>dec-2- (39) and -5-ene (59), respectively; 3) Thermal eliminative rearrangement of the 10endo-p-toluenesulfonate and -methanesulfonate of protoadamantane (71 and 72) and protoadamant-4-ene (76 and 77), respectively, yielding tricyclo4,8>dec-2-ene (39) and -2,5-diene (15), respectively.

ADAMANTANE REARRANGEMENT MECHANISM. 1,2-TRIMETHYLENENORBORNANES

Farcasiu, Malvina,Hagaman, Edward W.,Wenkert, Ernest,Schleyer, Paul von Rague

, p. 1501 - 1504 (1981)

Unexpected differences in the aluminium bromide-catalyzed rearrangement behavior of 1,2-endo-trimethylenenorbornane (1) and its 1,2-exo-isomer (2) are interpreted.Isotopic labelling studies indicate that reversible abstraction of the tertiary 2-endo hydride in 2 does not occur (Scheme 1).Instead, rearrangement to 6 is favored.The label scrambling in the final product, adamantane (8), is attributed to degenerate isomerization in the protoadamantyl precursor, 7.

Preparation and reactivity of a non-styrenic polymer-supported organotin chloride catalyst

Chemin, Alexandre,Deleuze, Herve,Maillard, Bernard

, p. 137 - 142 (1999)

A new type of macroporous polymer-supported organotin hydride has been prepared by suspension copolymerisation of an allyl ether monomer bearing an organotin moiety with N-phenylmaleimide and 1,1′-(methylenedi-4,1-phenylene)bismaleimide. Several resins were synthesised using different ratios of toluene-N-methylformanilide as the porogen. The swelling characteristics of the resins in different solvents and their specific surface areas were estimated. The organotin chloride-functionalised beads obtained showed good activity and good stability to reduction of bromoadamantane by sodium borohydride. Tin leaching during successive reuses was estimated.

THE THERMOLYSIS OF 1,1'-BIDIAMANTANE

Beckhaus, Hans-Dieter,Flamm, Manuela A.,Ruechardt, Christoph

, p. 1805 - 1808 (1982)

The activation parameters for the homolytic cleavage of the central CC-bond in 1.1'-bidiamantane 5 and their comparison with corresponding data for 2.2.3.3-tetramethylbutane 6 together with the strain enthalpies of 5 and 6 are conclusive experimental evidence for the absence of appreciable strain in 1-adamantyl radicals 3.This supports predictions made on the basis of calculations using a recently developed force field for radicals.

Robinson,Tarratt

, p. 5 (1968)

CATALYTIC REARRANGEMENT OF TETRAHYDRODICYCLOPENTADIENE TO ADAMANTANE OVER Y-ZEOLITE

Honna, Kosaku,Sugimoto, Michio,Shimizu, Nobuaki,Karisaki, Konomu

, p. 315 - 318 (1986)

Bifunctional rare-earth exchanged Y zeolite, has the high catalytic activity for the synthesis of adamantane from tetrahydrodicyclopentadiene in the presence of hydrogen and hydrogen chloride, in a fixed bed flow system.The catalyst deactivated by pore plugging with deposited hydrocarbons can be almost completely regenerated by hydrocracking.

A FACILE SYNTHESIS OF 3,4-HOMOADAMANTANEDIOL VIA THE REACTION OF 1-ADAMANTYL TRIFLATE WITH CARBON MONOXIDE

Takeuchi, Ken'ichi,Miyazaki, Tadakazu,Kitagawa, Itsuko,Okamoto, Kunio

, p. 661 - 664 (1985)

The reaction of 1-adamantyl triflate (1) with carbon monoxide and adamantane catalyzed by triflic acid affords 3-hydroxy-4-homoadamantyl 1-adamantanecarboxylate (2) as a major product, which is easily converted to 3,4-homoadamantanediol (5) - a promising starting material for 3,4-bifunctional homoadamantane derivatives.

Direct Hydrodecarboxylation of Aliphatic Carboxylic Acids: Metal- and Light-Free

Burns, David J.,Lee, Ai-Lan,McLean, Euan B.,Mooney, David T.

supporting information, p. 686 - 691 (2022/01/28)

A mild and inexpensive method for direct hydrodecarboxylation of aliphatic carboxylic acids has been developed. The reaction does not require metals, light, or catalysts, rendering the protocol operationally simple, easy to scale, and more sustainable. Crucially, no additional H atom source is required in most cases, while a broad substrate scope and functional group tolerance are observed.

Preparation method of adamantanone

-

Paragraph 0033; 0044-0047; 0052; 0063-0066; 0070; 0081-0084;, (2021/04/03)

The invention discloses a preparation method of adamantanone, and relates to the technical field of adamantanone synthesis. The problems that the reaction time is long and the operation process is tedious are solved. The preparation method specifically comprises the following steps: putting raw materials including adamantane, sulfuric acid and trifluoroacetic acid into a batching kettle, and stirring and mixing at 30 DEG C; raising the temperature to 50 DEG C, and introducing nitrogen into the batching kettle; pressing the mixed materials into a reaction tube, and performing standing for 1 minute; pouring the reaction solution on 500g of ice, adding a NaOH aqueous solution which is 7 times the weight of adamantane during cooling, and adjusting the pH value to 9; and extracting by using methylbenzene of which the weight is 3 times that of adamantane. The raw materials are mixed and then heated, nitrogen is introduced, then an oxidation reaction occurs, the retention time and temperatureof reaction liquid in a reaction tube are controlled in the leading-out period, the reaction liquid is extracted through methylbenzene and the NaOH aqueous solution, the extraction liquid is subjected to reduced pressure distillation concentration, cooling, separation and drying treatment, the final product is obtained, the operation process is relatively simple, the reaction is controllable, andthe time is short.

Photoredox catalysis on unactivated substrates with strongly reducing iridium photosensitizers

Shon, Jong-Hwa,Kim, Dooyoung,Rathnayake, Manjula D.,Sittel, Steven,Weaver, Jimmie,Teets, Thomas S.

, p. 4069 - 4078 (2021/04/06)

Photoredox catalysis has emerged as a powerful strategy in synthetic organic chemistry, but substrates that are difficult to reduce either require complex reaction conditions or are not amenable at all to photoredox transformations. In this work, we show that strong bis-cyclometalated iridium photoreductants with electron-rich β-diketiminate (NacNac) ancillary ligands enable high-yielding photoredox transformations of challenging substrates with very simple reaction conditions that require only a single sacrificial reagent. Using blue or green visible-light activation we demonstrate a variety of reactions, which include hydrodehalogenation, cyclization, intramolecular radical addition, and prenylationviaradical-mediated pathways, with optimized conditions that only require the photocatalyst and a sacrificial reductant/hydrogen atom donor. Many of these reactions involve organobromide and organochloride substrates which in the past have had limited utility in photoredox catalysis. This work paves the way for the continued expansion of the substrate scope in photoredox catalysis.

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