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294-62-2

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294-62-2 Usage

Overview

Cyclododecane (CDD) is an explosive cyclic alkane and is moderately inert since it is exclusively hydrogen and carbon compounds and is non-polar. The colorless, translucent compound has a wax-like consistency as well as good film-forming properties. At room temperature, cyclododecane is stable and is commonly sold in form of irregularly formed crystals. The compound has a boiling point of 243oC and a melting point of 58-61oC. The most attractive property of cyclododecane is that it sublimes, thus eliminating additional chemical procedures that can remove it. Studies have revealed that cyclododecane can sublime at the rate of 0.03 mm per 24 hours. Nevertheless, sublimation of cyclododecane is dependent on many factors such as film density and thickness, atmospheric pressure and temperature, substrate porosity, and air exchange over the film’s surface.

Uses

Different sources of media describe the Uses of 294-62-2 differently. You can refer to the following data:
1. Cyclododecane is considered as a new product in the conservation industry that is utilized as a temporary fixative, consolidant, barrier layer, and masking material in numerous fields of specialization. As a consolidant, it protects fragile ceramics while moving; therefore, allowing packaging and handling without any damage. As a temporary adhesive, cyclododecane has also been used remove subsequent of an adhesive without causing any damage. Its film-forming properties are one of the desirable working characteristics. The compound has been employed as a fixative for moisture-sensitive media on paper in the process of aqueous treatment. Due to its non-polar quality, cyclododecane can be used to protect materials that are solvent-sensitive during local solvent treatment. At room temperature, cyclododecane has the ability form a typically rigid solid, therefore, it has been used to secure friable substrates or flaking paint during transportation or during cleaning in surrounding. Moreover, it has been used to isolate the surface of an object when making mold.
2. Cyclooctane and cyclononane are used as starting materials for organic synthesis. The major use of cyclododecane is as an intermediate for the production of chemicals used to make polyamides, polyesters, synthetic lubricating oils, and nylon 12; it is also used as a high-purity solvent. An emulsion of cyclododecane can be used to emulsify pesticides. It is also used as a mothproofing agent.

Application Methods

Cyclododecane can be applied as a solvent solution or a melt. There should be a consideration of the substrate when selecting an application methods. Cyclododecane is generally reapplied between treatments for works of art paper. Cyclododecane melts at about 60oC and can applied with a wax-melting stylus, heated spatula, melting the compound, and spraying machine. A rheostat may be used to control the temperatures of the tools used to apply cyclododecane. Brush application should not be used unless a solvent is added at lower melting point. Cyclododecane will solidify and form a film after cooling. On the other hand, an immediate transition in temperature will form a dense, homogeneous film. Cyclododecane can be dissolved in aromatic and non-polar solvents and applied by syringe, brush, or aerosol-spray. However, it is almost impossible to produce uniform films and numerous applications are needed to build up the film. It is important to note that a film layer should be produced using a saturated solution. The concentration of solid will fluctuate with use of a heated stirring tool and the choice of solvent.

Treatment Considerations

It is important to evaluate the aims of the treatment and the stability of object. Also, sensitivity of object to hydrocarbon or to heat should be considered. Although CDD is comparatively transparent, areas that are normally covered with the compound have reduced clarity.

Health Effects

Contact of cyclododecane with the skin may cause rash or irritation while it can cause irritation and discomfort to the eye or a blurring vision. To avoid inhalation exposure through vapors, one should wear a respirator. Eye protection such as goggles and safety glasses is recommended to avoid contact through spraying or splashing of the material. In addition, gloves should always be used when handling cyclododecane solvents. As a volatile material, cyclododecane should be stored away from flames and sparks, which might ignite it. Moreover, it should not be mixed with strong oxidants.

Chemical Properties

Different sources of media describe the Chemical Properties of 294-62-2 differently. You can refer to the following data:
1. white solid
2. Cyclooctane and cyclononane are flammable liquids, and cyclododecane a volatile, flammable solid.

Synthesis Reference(s)

Tetrahedron Letters, 36, p. 3897, 1995 DOI: 10.1016/0040-4039(95)00593-2

Check Digit Verification of cas no

The CAS Registry Mumber 294-62-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,9 and 4 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 294-62:
(5*2)+(4*9)+(3*4)+(2*6)+(1*2)=72
72 % 10 = 2
So 294-62-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H24/c1-2-4-6-8-10-12-11-9-7-5-3-1/h1-12H2

294-62-2SDS

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 CYCLODODECANE

1.2 Other means of identification

Product number -
Other names Cyclododecane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:294-62-2 SDS

294-62-2Synthetic route

cyclododecene
1501-82-2

cyclododecene

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With aluminum oxide; sodium tetrahydroborate; nickel dichloride In hexane at 40℃; Catalytic hydrogenation;100%
With ethanol; lithium; nickel dichloride; 4,4'-di-tert-butylbiphenyl In tetrahydrofuran at 20℃; for 1h;99%
With hydrogen; NiCl2-Li-[poly(2-vinyl-naphthalene)-co-(divinylbenzene)] In tetrahydrofuran at 20℃; under 760.051 Torr; for 1h;99%
1-Chloro-2-phenylselanyl-cyclododecane

1-Chloro-2-phenylselanyl-cyclododecane

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride In tetrahydrofuran; methanol at 0℃; for 0.25h;100%
O-dodecyl S-methyl carbonodithioate
41320-42-7

O-dodecyl S-methyl carbonodithioate

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); hypophosphorous acid; sodium hydrogencarbonate In ethanol for 0.5h; Heating;100%
cyclododeca-1,5,9-triene
4904-61-4

cyclododeca-1,5,9-triene

A

cyclododecane
294-62-2

cyclododecane

B

cyclododecene
1501-82-2

cyclododecene

C

cyclododeca-1,5-diene
1502-04-1, 67881-13-4

cyclododeca-1,5-diene

Conditions
ConditionsYield
With hydrogen at 80 - 160℃; under 760.051 Torr; Reagent/catalyst; Flow reactor;A 100%
B n/a
C n/a
With hydrogen; Ru4Sn6/Davison 923 mesoporous silica at 119.84℃; under 22502.3 Torr; for 12h; Product distribution; Further Variations:; reaction times;
O-cyclododecyl-S-methyl dithiocarbonate
4373-12-0

O-cyclododecyl-S-methyl dithiocarbonate

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With air; trimethylborane; water In benzene at 20℃;99%
With di-tert-butyl peroxide; Diphenylphosphine oxide In 1,4-dioxane for 16h; Reduction; Heating;98%
With tris-(trimethylsilyl)silane; 1,1'-azobis(1-cyanocyclohexanenitrile) In water at 100℃; for 4h;98%
(1E,5E,9Z)-cyclododeca-1,5,9-triene
706-31-0

(1E,5E,9Z)-cyclododeca-1,5,9-triene

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With hydrogen at 240℃; under 760.051 Torr; Reagent/catalyst; Flow reactor;99%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 8h; Reagent/catalyst;> 99 %Chromat.
Thiocarbonic acid O-cyclododecyl ester O-(4-fluoro-phenyl) ester
130534-80-4

Thiocarbonic acid O-cyclododecyl ester O-(4-fluoro-phenyl) ester

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With tris-(trimethylsilyl)silane; triethyl borane; oxygen In benzene at 25℃; for 0.166667h; other reagent: diphenylsilane;98%
With triethyl borane; diphenylsilane; oxygen In hexane; benzene for 0.166667h; Ambient temperature;96%
With diphenylsilane; triethyl borane; oxygen In benzene at 25℃; for 0.166667h; Product distribution; Mechanism; same reaction of further thiocarbonyl compounds; other reagents (tris(trimethylsilyl)silane); other temp. and reaction times;96%
O-cyclododecyl O-phenyl thionocarbonate
121410-95-5

O-cyclododecyl O-phenyl thionocarbonate

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With 2,2'-azobis-(2,4-dimethylvaleronitrile); tri-n-butyl-tin hydride In tetrahydrofuran at 70℃; for 3h; Solvent; Time; Barton-McCombie Deoxygenation; Inert atmosphere;96%
With 2,2'-azobis(isobutyronitrile); (2,6-dimethoxy-1-methylcyclohexa-2,5-dienyl)triisopropylsilane In hexane for 15h; Heating;92%
With 2,2'-azobis(isobutyronitrile); (2,6-dimethoxy-1-methylcyclohexa-2,5-dienyl)triisopropylsilane In hexane for 15h; Heating;92%
O-cyclododecyl N-phenyl-thiocarbamate
157258-21-4

O-cyclododecyl N-phenyl-thiocarbamate

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); 9,10-dihydro-9,10-dimethyl-9,10-disilaanthracene In benzene for 2h; Heating;96%
With tris-(trimethylsilyl)silane; 1,1'-azobis(1-cyanocyclohexanenitrile) In water at 100℃; for 4h;85%
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In benzene at 80℃; for 0.5h;95 % Chromat.
With 5,10-dihydro-silanthrene; ABIN In toluene at 80℃; for 2h;32 % Chromat.
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In benzene at 80℃; for 0.5h; Mechanism; deoxygenation of various thioxocarbamate der. with variation of reagent and temp.;95 % Chromat.
(E)-Cyclododecen
1486-75-5

(E)-Cyclododecen

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With naphthalene; water-d2; lithium; nickel dichloride In tetrahydrofuran Ambient temperature;93%
1-cyclododecyloxymethylpyrrolidin-2-one

1-cyclododecyloxymethylpyrrolidin-2-one

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With 2,2-bis(tert-butylperoxy)butane; tri-tert-butoxysilanethiol In octane for 3h; Heating;93%
cyclododecanone
830-13-7

cyclododecanone

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With triethylsilane; 2C2H3F3O*BF3 In dichloromethane at 20℃; for 2.5h;92%
With hydrogenchloride; amalgamated zinc at 155℃;
triethyl borane
97-94-9

triethyl borane

O-cyclododecyl-S-methyl dithiocarbonate
4373-12-0

O-cyclododecyl-S-methyl dithiocarbonate

A

S-Ethyl S'-methyl dithiocarbonate
10596-55-1

S-Ethyl S'-methyl dithiocarbonate

B

cyclododecane
294-62-2

cyclododecane

C

cyclododecene
1501-82-2

cyclododecene

D

1,1'-bicyclododecane
88011-88-5

1,1'-bicyclododecane

E

cyclododecanone
830-13-7

cyclododecanone

Conditions
ConditionsYield
With air In hexane Product distribution; Mechanism; Ambient temperature; variation of temperature; other thiocarbonyl derivatives;A 91%
B 62%
C 12%
D 9%
E 4%
Acetyl-thiocarbamic acid O-cyclododecyl ester

Acetyl-thiocarbamic acid O-cyclododecyl ester

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With triethyl borane; HSiPh3 In benzene for 0.166667h; Ambient temperature;91%
cyclododecyl isocyanide
121282-62-0

cyclododecyl isocyanide

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With perhydrodibenzo-18-crown-6; potassium; toluene Ambient temperature;90%
O-cyclododecyl 1H-imidazole-1-carbothioate

O-cyclododecyl 1H-imidazole-1-carbothioate

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With tris-(trimethylsilyl)silane; 1,1'-azobis(1-cyanocyclohexanenitrile) In water at 100℃; for 4h;90%
With 5,10-dihydro-silanthrene; ABIN In toluene at 80℃; for 2h;46 % Chromat.
3-cyclododecyloxymethyloxazolidin-2-one

3-cyclododecyloxymethyloxazolidin-2-one

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With 2,2-bis(tert-butylperoxy)butane; tri-tert-butoxysilanethiol In octane for 3h; Heating;90%
cyclododecyl acetate
6221-92-7

cyclododecyl acetate

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With di-tert-butyl peroxide; (4-diphenylsilylphenyl)diphenylsilane at 140℃; for 15h;89%
With di-tert-butyl peroxide; (4-diphenylsilylphenyl)diphenylsilane at 140℃; for 15h; Product distribution; alcohol deoxygenation via acetate; reaction with Ph3SiH;89%
With di-tert-butyl peroxide; diphenylsilane at 140℃; for 20h;75 % Chromat.
2-Cyclododecylsulfanyl-benzothiazole
109275-15-2

2-Cyclododecylsulfanyl-benzothiazole

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) In benzene for 14h; Heating;89%
1,3,7,9-cyclododecatetrayne
4728-87-4

1,3,7,9-cyclododecatetrayne

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With hydrogen; platinum In ethyl acetate at 20℃; for 12h;86%
cis-cyclododecene
1129-89-1

cis-cyclododecene

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With magnesium; palladium on activated charcoal In methanol Ambient temperature;85%
With hydrogen; alkylated polyethyleneimine; palladium In water at 80℃; under 1500.12 Torr; for 5h;
cyclododecyl bromide
7795-35-9

cyclododecyl bromide

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With water; zinc In acetonitrile at 80℃; for 4h; Sealed tube; Inert atmosphere;84%
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; isopropyl alcohol In tetrahydrofuran for 0.166667h; Ambient temperature; Yield given;
With zinc; cob(I)alamin In water; acetic acid for 93h; Ambient temperature; Yield given;
cyclododecyl acetate
6221-92-7

cyclododecyl acetate

HSiPh3
789-25-3

HSiPh3

A

cyclododecane
294-62-2

cyclododecane

B

triphenylsilyl acetate
1929-33-5

triphenylsilyl acetate

Conditions
ConditionsYield
With di-tert-butyl peroxide at 140℃; for 12h;A 82%
B n/a
1,2-epoxy-5,9-cyclododecadiene
943-93-1

1,2-epoxy-5,9-cyclododecadiene

A

cyclododecane
294-62-2

cyclododecane

B

cyclododecanol
1724-39-6

cyclododecanol

C

cyclododecanone
830-13-7

cyclododecanone

D

1,2-epoxycyclododecane
286-99-7

1,2-epoxycyclododecane

Conditions
ConditionsYield
With hydrogen; palladium on silica gel at 160 - 175℃; under 2205.22 - 6615.66 Torr; for 2 - 5h;A 0.2%
B 0.9%
C 81.6%
D 10.6%
With hydrogen; Pd/silica-alumina at 160℃; under 6615.66 Torr; for 2h;A 0.3%
B 2.4%
C 70.7%
D 25.5%
With hydrogen; 5 wt percent Pd/zeolite at 160℃; under 6615.66 Torr; for 2h;A 0.5%
B 1.8%
C 69.4%
D 27.5%
Hexanoic acid cyclododecyl ester
76733-12-5

Hexanoic acid cyclododecyl ester

HSiPh3
789-25-3

HSiPh3

A

cyclododecane
294-62-2

cyclododecane

B

C24H26O2Si

C24H26O2Si

Conditions
ConditionsYield
With di-tert-butyl peroxide at 140℃; for 12h;A 81%
B n/a
cyclododecyl methyl xanthate

cyclododecyl methyl xanthate

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With diphenylsilane; triethyl borane; oxygen In benzene at 25℃; for 0.166667h;81%
N-4-fluorophenylthioxocarbamate of cyclododecanol

N-4-fluorophenylthioxocarbamate of cyclododecanol

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In benzene at 80℃;76%
cyclododecyl methoxymethyl ether
42604-12-6

cyclododecyl methoxymethyl ether

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With 2,2-bis(tert-butylperoxy)butane; tri-tert-butoxysilanethiol In octane for 3h; Heating;74%
cyclododecyl p-nitrophenyl selenide
94473-30-0

cyclododecyl p-nitrophenyl selenide

cyclododecane
294-62-2

cyclododecane

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride In tetrahydrofuran; methanol at 0℃; for 0.25h;71%
(1E,5E,9Z)-cyclododeca-1,5,9-triene
706-31-0

(1E,5E,9Z)-cyclododeca-1,5,9-triene

A

cyclododecane
294-62-2

cyclododecane

B

cyclododecene
1501-82-2

cyclododecene

Conditions
ConditionsYield
With hydrogen at 240℃; under 760.051 Torr; Reagent/catalyst; Flow reactor;A 71%
B 26%
cyclododecane
294-62-2

cyclododecane

chlorocyclododecane
34039-83-3

chlorocyclododecane

Conditions
ConditionsYield
With N-chloro-succinimide; benzophenone In acetonitrile at 27℃; for 24h; Reagent/catalyst; Irradiation; regioselective reaction;95%
With tetrachloromethane at 250℃; for 7h; Inert atmosphere; Autoclave;35%
With methanol; tetrachloromethane; molybdenum hexacarbonyl at 170℃; for 1h; Temperature; Time; Sealed tube;
quinoxalin-2(1)-one
1196-57-2

quinoxalin-2(1)-one

cyclododecane
294-62-2

cyclododecane

3-cyclododecylquinoxalin-2(1H)-one

3-cyclododecylquinoxalin-2(1H)-one

Conditions
ConditionsYield
With di-tert-butyl peroxide In 1,2-dichloro-ethane at 130℃; for 4h; Sealed tube;93%
cyclododecane
294-62-2

cyclododecane

6-methoxyquinaldine
1078-28-0

6-methoxyquinaldine

4-cyclododecyl-6-methoxy-2-methylquinoline

4-cyclododecyl-6-methoxy-2-methylquinoline

Conditions
ConditionsYield
With trifluoroacetic acid; dibenzoyl peroxide In 1,2-dichloro-ethane at 100℃; for 4h; Inert atmosphere;92%
cyclododecane
294-62-2

cyclododecane

A

cyclododecane-1,7-diol
13474-06-1

cyclododecane-1,7-diol

B

1,6-cyclododecanediol
14435-21-3

1,6-cyclododecanediol

Conditions
ConditionsYield
With cytochrome P450 enzyme CYP101B1 In aq. buffer pH=7.4; Kinetics; Reagent/catalyst; Enzymatic reaction;A 92%
B n/a
C6H4NCH2CHCCH2
491-35-0

C6H4NCH2CHCCH2

cyclododecane
294-62-2

cyclododecane

2-cyclododecyl-4-methylquinoline

2-cyclododecyl-4-methylquinoline

Conditions
ConditionsYield
With hydrogenchloride; Selectfluor In water; acetone at 20℃; for 16h; Inert atmosphere; Irradiation;90%
With trifluoroacetic acid; dibenzoyl peroxide In 1,2-dichloro-ethane at 100℃; for 4h; Inert atmosphere;78%
cyclododecane
294-62-2

cyclododecane

bis(2,2,2-trichlorethyl)azodicarboxylate
38857-88-4

bis(2,2,2-trichlorethyl)azodicarboxylate

C18H28Cl6N2O4
1407999-64-7

C18H28Cl6N2O4

Conditions
ConditionsYield
With N-hydroxyphthalimide In 1,2-dichloro-ethane at 20 - 80℃; for 5h; Inert atmosphere; chemoselective reaction;87%
2-Chloroquinoline
612-62-4

2-Chloroquinoline

cyclododecane
294-62-2

cyclododecane

2-chloro-4-cyclododecylquinoline

2-chloro-4-cyclododecylquinoline

Conditions
ConditionsYield
With 2,2,2-trifluoroethanol; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 17h; Reagent/catalyst; Minisci Aromatic Substitution; Inert atmosphere; Irradiation; Green chemistry;86%
phenylacetic acid
103-82-2

phenylacetic acid

cyclododecane
294-62-2

cyclododecane

cyclododecyl 2-phenylacetate
42463-71-8

cyclododecyl 2-phenylacetate

Conditions
ConditionsYield
With 2,2,6,6-tetramethylpiperidinium triflate In neat liquid at 120℃; for 12h; Reagent/catalyst; Green chemistry;85%
cyclododecane
294-62-2

cyclododecane

para-thiocresol
106-45-6

para-thiocresol

(cyclododecyl)(4-methylphenyl)sulfide

(cyclododecyl)(4-methylphenyl)sulfide

Conditions
ConditionsYield
With N-Bromosuccinimide; di-tert-butyl peroxide; Bathocuproine; nickel(II) acetate tetrahydrate In fluorobenzene at 140℃; for 24h; Inert atmosphere;85%
With di-tert-butyl peroxide; Bathocuproine; nickel(II) acetate tetrahydrate at 140℃; for 24h; Inert atmosphere; Schlenk technique;82%

294-62-2Relevant articles and documents

Saltiel,J.,Ng Lim,L.-S.

, p. 5404 - 5405 (1969)

Diastereomeric cyclic tris-allenes

Mustafa, Hussein H.,Baird, Mark S.,Al Dulayymi, Juma'A R.,Tverezovskiy, Viacheslav V.

, p. 2497 - 2499 (2013)

Both diastereomers of the tris-allene, cyclododeca-1,2,5,6,9,10-hexaene have been obtained using a triple cyclopropylidene-allene rearrangement. On the NMR timescale, one has D3 symmetry, and is the smallest hydrocarbon synthesised to have this symmetry, and the second has C2 symmetry.

Discrimination of Rotational Isomeric States in Cycloalkanes by Solid-State CP-MAS 13C NMR Spectroscopy

Moeller, Martin,Gronski, Wolfram,Cantow, Hans Joachim,Hoecker, Hartwig

, p. 5093 - 5099 (1984)

The solid-state behavior of three cycloalkanes, cyclododecane, cyclotetraeicosane, and cyclohexatriacontane, was investigated by means of temperature dependent magic angle cross-polarization 13C NMR experiments.For the two smaller ring molecules a state of high internal mobility like the "rotator phase" in n-alkanes was detected.It could be correlated with a phase transition in the solid state visible by means of DSC.In the case of (CH2)12 this is 151 K below the melting point, and in the case of (CH2)24 it is 25 K below the melting transition.The CP-MAS 13C NMR spectra show a transition from the fast exchange to the slow exchange regime of magnetically nonequivalent states.By comparison with X-ray diffraction data the well-resolved resonance signals for the low-temperature phases were assigned to molecular segments distinguished by the rotational isomeric states of the carbon-carbon bonds.Chemical shift differences due to conformational isomerism were as large as 12 ppm; thus, they exceed "packing effects" by far.

Sustainable System for Hydrogenation Exploiting Energy Derived from Solar Light

Ishida, Naoki,Kamae, Yoshiki,Ishizu, Keigo,Kamino, Yuka,Naruse, Hiroshi,Murakami, Masahiro

supporting information, p. 2217 - 2220 (2021/02/16)

Herein described is a sustainable system for hydrogenation that uses solar light as the ultimate source of energy. The system consists of two steps. Solar energy is captured and chemically stored in the first step; exposure of a solution of azaxanthone in ethanol to solar light causes an energy storing dimerization of the ketone to produce a sterically strained 1,2-diol. In the second step, the chemical energy stored in the vicinal diol is released and used for hydrogenation; the diol offers hydrogen onto alkenes and splits back to azaxanthone, which is easily recovered and reused repeatedly for capturing solar energy.

A New Protocol for Catalytic Reduction of Alkyl Chlorides Using an Iridium/Bis(benzimidazol-2′-yl)pyridine Catalyst and Triethylsilane

Fukuyama, Takahide,Hamada, Yuki,Ryu, Ilhyong

, p. 3404 - 3408 (2021/07/14)

The reduction of alkyl chlorides using triethylsilane is investigated. Primary, secondary, tertiary, and benzylic C-Cl bonds are effectively converted into C-H bonds using an [IrCl(cod)] 2/2,6-bis(benzimidazol-2′-yl)pyridine catalyst system. This catalyst system is quite simple since the tridentate N-ligand can be easily prepared in one step from commercially available reagents.

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