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121-46-0 Usage

Chemical Properties

2,5-Norbornadiene, also known as dicycloheptadiene, is a clear colorless to slightly yellow liquid that is soluble in petroleum ether and insoluble in water. Commercially available goods usually contain 500 ppm of 2,6-di-tert-butyl-p-methylphenol (BHT) as a stabilizer. Analyzing the structural characteristics of NBD, it can be found that it has good reaction properties and can synthesize a variety of organic compounds through addition or substitution reactions at the double bond.

Uses

Different sources of media describe the Uses of 121-46-0 differently. You can refer to the following data:
1. 2,5-Norbornadiene has an anti-ethylene effect on plants and inhibits polyphenol oxidase, peroxidase and phenylalanine ammonia lyase activities.
2. 2,5-Norbornadiene is used as an intermediate in prostaglandin synthesis and shows anti-ethylene effect on plants. It acts as a starting material for the synthesis of diamantane and as an acetylene transfer agent for instance, in reaction with 3,6-di-2-pyridyl-1,2,4,5-tetrazine. It is also a useful dienophile in Diels-Alder reactions.

Preparation

2,5-Norbornadiene is of interest as a metal-binding ligand, whose complexes are useful for homogeneous catalysis. Norbornadiene can be formed by a Diels-Alder reaction between cyclopentadiene and acetylene.

General Description

2,5-norbornadiene, stabilized appears as a colorless liquid. Insoluble in water and less dense than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion, inhalation and skin absorption. When heated will polymerize and at decomposition emits acrid smoke and irritating fumes.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

2,5-NORBORNADIENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. Violent explosions at low temperatures in ammonia synthesis gas units have been traced to the addition products of dienes and nitrogen dioxide [Bretherick, 5th Ed., 1995].

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by inhalation. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Purify the diene by distillation from activated alumina [Landis & Halpern J Am Chem Soc 109 1746 1987]. [Beilstein 5 IV 879.]

Check Digit Verification of cas no

The CAS Registry Mumber 121-46-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 1 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 121-46:
(5*1)+(4*2)+(3*1)+(2*4)+(1*6)=30
30 % 10 = 0
So 121-46-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H8/c1-2-7-4-3-6(1)5-7/h1-2H,3-5H2

121-46-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Packaging
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  • Detail
  • TCI America

  • (N0346)  2,5-Norbornadiene (stabilized with BHT)  >97.0%(GC)

  • 121-46-0

  • 25mL

  • 330.00CNY

  • Detail
  • TCI America

  • (N0346)  2,5-Norbornadiene (stabilized with BHT)  >97.0%(GC)

  • 121-46-0

  • 100mL

  • 990.00CNY

  • Detail
  • TCI America

  • (N0346)  2,5-Norbornadiene (stabilized with BHT)  >97.0%(GC)

  • 121-46-0

  • 500mL

  • 3,480.00CNY

  • Detail
  • Alfa Aesar

  • (L13935)  2,5-Norbornadiene, 97%, stab with 250 ppm BHT   

  • 121-46-0

  • 25ml

  • 301.0CNY

  • Detail
  • Alfa Aesar

  • (L13935)  2,5-Norbornadiene, 97%, stab with 250 ppm BHT   

  • 121-46-0

  • 100ml

  • 765.0CNY

  • Detail
  • Aldrich

  • (B33803)  Bicyclo[2.2.1]hepta-2,5-diene  98%

  • 121-46-0

  • B33803-5ML

  • 358.02CNY

  • Detail
  • Aldrich

  • (B33803)  Bicyclo[2.2.1]hepta-2,5-diene  98%

  • 121-46-0

  • B33803-100ML

  • 2,027.61CNY

  • Detail
  • Aldrich

  • (B33803)  Bicyclo[2.2.1]hepta-2,5-diene  98%

  • 121-46-0

  • B33803-500ML

  • 4,578.21CNY

  • Detail

121-46-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name (1s,4s)-Bbicyclo[2.2.1]hepta-2,5-diene

1.2 Other means of identification

Product number -
Other names 2,5-Norbornadiene

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:121-46-0 SDS

121-46-0Synthetic route

quadricyclo[2.2.1.0.0]heptane
278-06-8

quadricyclo[2.2.1.0.0]heptane

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
x In nitromethane at 25℃;100%
cadmium(II) sulphide In dichloromethane for 3h; Product distribution; Irradiation; other semiconducters, presence of methylviologen dication and diphenylamine;1.8%
3,3-dimethyldioxirane In dichloromethane; acetone at 0℃; for 0.0166667h;60 % Turnov.
tetracyclo-[3.2.0.0.2,7.04,6]heptane
278-06-8

tetracyclo-[3.2.0.0.2,7.04,6]heptane

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With 1-Cyanonaphthalene In methanol Irradiation;
dichloro(norbornadiene)palladium(II) In dichloromethane at 25℃; for 1h; Product distribution; Quantum yield; Mechanism; Irradiation; different Q concentration, solvent, times, intensity and wavelenght of irradiation, effect of free radical scavenger;
With 9,10-Dicyanoanthracene In hexane Quantum yield; Mechanism; Rate constant; Ambient temperature; Irradiation; exciplex isomerization, var. of sensitizer, solv.;
With aluminum oxide; 4-Aminosalicylic acid; tetrasodium (5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrinato)cobalt(II) In pentane at 24℃; Rate constant; Thermodynamic data; ΔH(activation);
With trichlorostannylacetylene at 25℃; for 1h; Inert atmosphere;
(+-)-dimethyl-norborn-5-ene-2exo-yl-amine oxide

(+-)-dimethyl-norborn-5-ene-2exo-yl-amine oxide

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
at 200℃; under 30 - 60 Torr;
(+-)-trimethyl-norborn-5-ene-2exo-yl-ammonium hydroxide

(+-)-trimethyl-norborn-5-ene-2exo-yl-ammonium hydroxide

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
at 110 - 125℃; under 30 - 60 Torr;
endo-2,3-bis(phenylsulfonyl)bicyclo<2.2.1>hept-5-ene
27770-83-8

endo-2,3-bis(phenylsulfonyl)bicyclo<2.2.1>hept-5-ene

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With methanol; sodium dihydrogenphosphate; sodium amalgam Ambient temperature;65%
With sodium dihydrogenphosphate; sodium amalgam In methanol Ambient temperature;65%
exo-3-deuteriobicyclo<2.2.1>hept-5-enyl tosylate
132856-14-5

exo-3-deuteriobicyclo<2.2.1>hept-5-enyl tosylate

A

<2-D>Bicyclo<2.2.1>hepta-2,5-dien
74773-67-4, 92076-23-8

<2-D>Bicyclo<2.2.1>hepta-2,5-dien

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With 18-crown-6 ether; potassium tert-butylate In various solvent(s) at 60℃; Yield given. Yields of byproduct given;
With 18-crown-6 ether; potassium tri-2-norbornylmethoxide In various solvent(s) at 60℃; Yield given. Yields of byproduct given;
bicyclo<2.2.1>hepta-2,5-dien-2-yl p-tolyl sulfone
75612-58-7

bicyclo<2.2.1>hepta-2,5-dien-2-yl p-tolyl sulfone

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With sodium dihydrogenphosphate; sodium amalgam In methanol at 18℃;27%
quadricyclo[2.2.1.0.0]heptane
278-06-8

quadricyclo[2.2.1.0.0]heptane

A

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

exo-3-Oxa-4-thiatricyclo<4.2.1.02,5>non-7-ene 4-oxide

exo-3-Oxa-4-thiatricyclo<4.2.1.02,5>non-7-ene 4-oxide

Conditions
ConditionsYield
With sulfur dioxide In chloroform at 0℃; under 15 Torr; rotaevaporation;
tetracyclo-[3.2.0.0.2,7.04,6]heptane
278-06-8

tetracyclo-[3.2.0.0.2,7.04,6]heptane

A

7anti-Methoxy-norbornen-(2)
13041-10-6

7anti-Methoxy-norbornen-(2)

3-methoxynortricyclene
21516-65-4

3-methoxynortricyclene

C

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With Rh(pnen)3(3+) In methanol Irradiation;A n/a
B n/a
C 72%
exo-3,4-diazotricyclo[4.2.1.02,5]nona-3,7-diene
23979-29-5

exo-3,4-diazotricyclo[4.2.1.02,5]nona-3,7-diene

A

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

B

quadricyclo[2.2.1.0.0]heptane
278-06-8

quadricyclo[2.2.1.0.0]heptane

Conditions
ConditionsYield
With 9,10-Dicyanoanthracene Irradiation;
With 9,10-Dicyanoanthracene In acetonitrile at 23℃; Product distribution; Mechanism; Irradiation; var. sensitizers and solvents;
In various solvent(s) at 144.85℃; Kinetics; Further Variations:; Temperatures;
methanol
67-56-1

methanol

tetracyclo-[3.2.0.0.2,7.04,6]heptane
278-06-8

tetracyclo-[3.2.0.0.2,7.04,6]heptane

A

7anti-Methoxy-norbornen-(2)
13041-10-6

7anti-Methoxy-norbornen-(2)

3-methoxynortricyclene
21516-65-4

3-methoxynortricyclene

C

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With Rh(pnen)3(3+) In methanol Irradiation; Yield given. Title compound not separated from byproducts;A n/a
B n/a
C 72%
3,4-diazaquadricyclo[6.1.0.02,605,9]non-3-ene
16104-45-3

3,4-diazaquadricyclo[6.1.0.02,605,9]non-3-ene

A

tetracyclo-[3.2.0.0.2,7.04,6]heptane
278-06-8

tetracyclo-[3.2.0.0.2,7.04,6]heptane

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With Rh(pnen)3(3+) In acetonitrile Irradiation;A 47%
B 50%
(+-)-5endo,6exo-dichloro-norbornene

(+-)-5endo,6exo-dichloro-norbornene

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With diethyl ether; magnesium iodide
5endo,6endo-dichloro-norbornene

5endo,6endo-dichloro-norbornene

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
With diethyl ether; magnesium iodide
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

carbon monoxide
201230-82-2

carbon monoxide

A

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

B

molybdenum hexacarbonyl
13939-06-5, 199620-15-0

molybdenum hexacarbonyl

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter; CO pressure: 500 psi;A n/a
B 100%
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

1,3-bis-(diphenylphosphino)propane
6737-42-4

1,3-bis-(diphenylphosphino)propane

A

tetracarbonyl-1,3-bis(diphenylphosphino)propane-molybdenum(0)
15553-68-1

tetracarbonyl-1,3-bis(diphenylphosphino)propane-molybdenum(0)

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

bis-diphenylphosphinomethane
2071-20-7

bis-diphenylphosphinomethane

A

tetracarbonyl-bis(diphenylphosphino)methane-molybdenum(0)
26743-81-7

tetracarbonyl-bis(diphenylphosphino)methane-molybdenum(0)

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

trimethylphosphane
594-09-2

trimethylphosphane

cis-bis(trimethylphosphine)tetracarbonylmolybdenum
16027-45-5

cis-bis(trimethylphosphine)tetracarbonylmolybdenum

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

bis(trichlorophosphine)molybdenum tetracarbonyl
16244-51-2

bis(trichlorophosphine)molybdenum tetracarbonyl

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
pyridine
110-86-1

pyridine

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

cis-{molybdenum(0)(carbonyl)4(pyridine)2}
16742-99-7, 33570-29-5

cis-{molybdenum(0)(carbonyl)4(pyridine)2}

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
1,5-cis,cis-cyclooctadiene
1552-12-1, 111-78-4

1,5-cis,cis-cyclooctadiene

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

A

tetracarbonyl(1,5-cyclooctadiene)molybdenum
12109-74-9

tetracarbonyl(1,5-cyclooctadiene)molybdenum

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

1,2-Bis(diphenylphosphino)benzene
13991-08-7

1,2-Bis(diphenylphosphino)benzene

A

(1,2-bis(diphenylphosphino)benzene)molybdenum tetracarbonyl
111189-30-1

(1,2-bis(diphenylphosphino)benzene)molybdenum tetracarbonyl

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

A

(bis(dimethylphosphino)methane)molybdenum tetracarbonyl
90624-09-2

(bis(dimethylphosphino)methane)molybdenum tetracarbonyl

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

bis(trimethylphosphite)molybdenum tetracarbonyl
15631-22-8

bis(trimethylphosphite)molybdenum tetracarbonyl

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

triethylphosphine
554-70-1

triethylphosphine

cis-{molybdenum(0)(carbonyl)4(P(ethyl)3)2}
19217-80-2, 19217-81-3, 22614-45-5

cis-{molybdenum(0)(carbonyl)4(P(ethyl)3)2}

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran under argon; reaction in a calorimeter;A 100%
B n/a
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

triethylarsine
617-75-4

triethylarsine

bis(triethylarsine)molybdenum tetracarbonyl
111265-67-9

bis(triethylarsine)molybdenum tetracarbonyl

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran under argon; reaction in a calorimeter;A 100%
B n/a
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

A

(N,N,N',N'-tetramethylethylenediamine)tetracarbonylmolybdenum(0)
23301-98-6

(N,N,N',N'-tetramethylethylenediamine)tetracarbonylmolybdenum(0)

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

1,2-bis(dimethylphosphanyl)ethane
23936-60-9

1,2-bis(dimethylphosphanyl)ethane

A

(1,2-bis(dimethylphosphino)ethane)molybdenum tetracarbonyl
40544-97-6

(1,2-bis(dimethylphosphino)ethane)molybdenum tetracarbonyl

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

di(cyclohexylisocyanide)molybdenum tetracarbonyl
15227-72-2

di(cyclohexylisocyanide)molybdenum tetracarbonyl

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran under argon; reaction in a calorimeter;A 100%
B n/a
2.9-dimethyl-1,10-phenanthroline
484-11-7

2.9-dimethyl-1,10-phenanthroline

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
12146-37-1, 124717-04-0

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

A

molybdenum(0) tetracarbonyl(2,9-dimethyl-1,10-phenanthroline)
23301-98-6

molybdenum(0) tetracarbonyl(2,9-dimethyl-1,10-phenanthroline)

B

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

Conditions
ConditionsYield
In tetrahydrofuran reaction in a calorimeter under argon;A 100%
B n/a
bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

hex-1-yne
693-02-7

hex-1-yne

Conditions
ConditionsYield
With diphosphane; (2S,3S)-(+)-bis(diphenylphosphanyl)bicyclo[2.2.1]hept-5-ene; cobalt(III) acetylacetonate; diethylaluminium chloride In tetrahydrofuran at 35℃; for 4h;100%
bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

phenylacetylene
536-74-3

phenylacetylene

C15H14

C15H14

Conditions
ConditionsYield
With cobalt(III) acetylacetonate; diethylaluminium chloride; 1,2-bis-(diphenylphosphino)ethane In toluene; benzene Ambient temperature;100%
bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

4-Aza-2-oxo-1-oxaspiro<5.4>dec-3-ene 4-oxide
155052-20-3

4-Aza-2-oxo-1-oxaspiro<5.4>dec-3-ene 4-oxide

rel-(5aR,6R,9S,9aR,9bS)-7,8-dehydro-6,9-methano-1-oxo-1,5a,9a,9b-tetrahydrocyclohex[f]isoxazolo[2,3-c]oxazole-3-spiro-1'-cyclohexane

rel-(5aR,6R,9S,9aR,9bS)-7,8-dehydro-6,9-methano-1-oxo-1,5a,9a,9b-tetrahydrocyclohex[f]isoxazolo[2,3-c]oxazole-3-spiro-1'-cyclohexane

Conditions
ConditionsYield
for 9h; Ambient temperature;100%
1-Heptyne
628-71-7

1-Heptyne

carbon monoxide
201230-82-2

carbon monoxide

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

(3aR,4S,7R,7aR)-2-Pentyl-3a,4,7,7a-tetrahydro-4,7-methano-inden-1-one
85806-43-5, 85806-49-1, 122422-23-5, 122422-24-6

(3aR,4S,7R,7aR)-2-Pentyl-3a,4,7,7a-tetrahydro-4,7-methano-inden-1-one

Conditions
ConditionsYield
dodecacarbonyl tetracobalt In dichloromethane at 150℃; under 7600 Torr; for 6h;100%
Co/C In tetrahydrofuran at 130℃; under 22800 Torr; for 18h; Pauson-Khand reaction;98%
Pauson-Khand reaction;64%
4-(2-bromo-phenyl)-1-methyl-1H-pyrrole-3-carboxylic acid ethyl ester
938164-26-2

4-(2-bromo-phenyl)-1-methyl-1H-pyrrole-3-carboxylic acid ethyl ester

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

C16H15NO2

C16H15NO2

Conditions
ConditionsYield
With caesium carbonate; palladium diacetate; triphenylphosphine In toluene at 120℃;100%
2-Bromobiphenyl
2052-07-5

2-Bromobiphenyl

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

C19H16

C19H16

Conditions
ConditionsYield
With caesium carbonate; palladium diacetate; triphenylphosphine In toluene at 130℃;100%
silver tetrafluoroborate
14104-20-2

silver tetrafluoroborate

bis(ethylene)rhodium(I) chloride dimer

bis(ethylene)rhodium(I) chloride dimer

bicyclo[2.2.1]hepta-2,5-diene
121-46-0

bicyclo[2.2.1]hepta-2,5-diene

di(norbornadiene)rhodium(I) tetrafluoroborate

di(norbornadiene)rhodium(I) tetrafluoroborate

Conditions
ConditionsYield
In dichloromethane under N2 or Ar, addn. of diene in CH2Cl2 to Rh-complex in CH2Cl2, then addn. of solid AgBF4, soln. is stirred for 45 min; filtn. through Celite, addn. of THF to the filtrate, concn., filtn. of deep red crystals, washed with THF, air-dried;100%

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121-46-0Relevant articles and documents

SURFACE PHOTOCHEMISTRY: SEMICONDUCTOR PHOTOINDUCED VALENCE ISOMERIZATION OF QUADRICYCLANE TO NORBORNADIENE

Draper, Anthony M.,Mayo, Paul de

, p. 6157 - 6160 (1986)

Contrary to a recent report, the valence isomerization via a radical cation, of quadricyclane to norbornadiene on the surface of illuminated CdS and ZnO is described.

Iridium-Catalyzed Asymmetric Hydroalkenylation of Norbornene Derivatives

Sun, Xin,Bai, Xiao-Yan,Li, An-Zhen,Li, Bi-Jie

, p. 2182 - 2187 (2021)

Transition-metal-catalyzed asymmetric hydroalkenylation of alkenes provides an atom-economical method to build molecular complexity from easily available materials. Herein we report an iridium-catalyzed asymmetric hydroalkenylation of unconjugated alkenes with acrylamides and acrylates. The catalytic hydroalkenylation of norbornene derivatives occurred to form products with allylic stereocenters with high chemo-, regio-, and stereoselectivities. DFT calculations revealed that the migratory insertion is irreversible and the enantiodetermination step.

Structure-Reactivity Factors for Exciplex Isomerization of Quadricyclene and Related Compounds

Jones, Guilford,Chiang, Sheau-Hwa,Becker, William G.,Greenberg, Don P.

, p. 681 - 683 (1980)

The quadricyclenes (1) and (3) are equally effective in exciplex isomerization although other cage hydrocarbons do not undergo efficient reaction when sensitized by aromatic fluorophores; irradiation of charge-transfer complexes of (1) and (3) and electron-deficient alkenes results in efficient valence but not geometrical isomerization.

-

Wiberg,Connon

, p. 5411,5412 (1976)

-

THERMAL ISOMERIZATION OF QUADRICYCLANE TO NORBORNADIENE CATALYZED BY COPPER(II) AND TIN(II) SALTS.

Fife,Morse,Moore

, p. 7404 - 7407 (1983)

Copper(II) salts and tin(II) chloride show exceptional heterogeneous catalytic behavior in converting quadricyclane to norbornadiene in benzene. The heterogeneous catalysis mechanism is described by the adsorption of quadricyclane on the salt surface by a combination of a one-site and a two-site coordination. The two-site-coordination process results in the formation of C//7H//8X//2 (X equals Cl or Br) as a side product when CuCl//2 or CuBr//2 are used as catalysts. The rate constant for the disappearance of quadricyclane is much greater when CuCl//2 or CuBr//2 are used as catalysts. The rate constant for the disappearance of quadricyclane is much greater when CuCl//2 or CuBr//2 (approximately 10** minus **2 min** minus **1 cm** minus **2) is used than when CuSO//4 (approximately 10** minus **4 min** minus **1 cm** minus **2) is used.

PHOTOGENERATED CATALYSIS BY TRANSITION-METAL COMPLEXES. PHOTOACCELERATION OF THE VALENCE ISOMERIZATION OF QUADRICYCLENE TO NORBORNADIENE IN THE PRESENCE OF PdCl2( eta 4-NORBORNADIENE).

Borsub,Kutal

, p. 4826 - 4828 (1984)

Light accelerates the rate at which PdCl//2( eta **4-NBD) (1) catalyzes the valence isomerization of quadricyclene (Q) to norbornadiene (NBD). The observed quantum yield, defined as (mol of NBD produced/mol of photons absorbed), can exceed 10**2 and is dependent upon Q concentration, light intensity, and solvent. Several lines of evidence are consistent with the intermediacy of radical species in the isomerization process. The results are discussed in terms of a redox-chain mechanism in which the initiation step involves reductive quenching of a Pd-to-NBD charge-transfer excited state of 1 by Q.

Chemistry of Weakly Solvated Lanthanide-Metal Cations. Synthesis, Characterization, and Catalytic Chemistry of x

Thomas, Richard R.,Chebolu, Venkatasuryanarayana,Sen, Ayusman

, p. 4096 - 4103 (1986)

The title compound, x, 1, was synthesized by the NOBF4 oxidation of metallic Eu in CH3CN.The interaction of the BF4- ions with the Eu(III) center was established by molecular weight, conductivity, and 11B and 19F NMR spectral measurements. 1 was found to exist as a dimer in CH3CN.In addition, it behaved as a 1:2 electrolyte, indicating the coordination of two of the BF4- ions per Eu(III) ion.However, the conductivity increased when chelating amines were added due to the partial displacement of the coordinated BF4- ions.The 11B and 19F NMR spectra of 1 in CH3CN indicated the presence of two different types of BF4- anions, one of which was isotropically shifted due to interaction with the paramagnetic Eu(III) center.The coordinated BF4- anions could be displaced quantitatively by the addition of 2 equiv of NO3- ions per Eu(III) ion.A degenerate metathesis of the fluorine between the BF3 and the coordinated BF4- ions was observed when BF3 was added to a CH3CN solution of 1. 1 formed a charge-transfer complex with tetra-p-anisylethylene in CH3NO2 but not in CH3CN.In addition, 1 initiated the oligomerization and the polymerization of styrene, α-methylstyrene, and 1,3-cyclohexadiene in CH3NO2.The molecular weights of the polymers obtained increased markedly on lowering the reaction temperature.At room temperature, indan derivatives were obtained from α-methyl- and α-phenylstyrene.The rate of polymerization of styrene was markedly attenuated when CH3CN was used instead of CH3NO2. 1 also initiated the isomerization of quadricyclane and the ring-opening polymerization of 2(10)-pinene and cyclopropylbenzene in CH3NO2.

Fourier transform near-infrared absorption spectroscopic study of catalytic isomerization of quadricyclane to norbornadiene by copper(II) and tin(II) salts

Chuang, Eric Chau-Chin,Lin, King-Chuen

, p. 132 - 136 (2002)

By using Fourier transform near-infrared (NIR) absorption spectroscopy, we have investigated the catalytic conversion of quadricyclane to norbornadiene. Either CuSO4 in chloroform or SnCl2 in benzene is used as catalyst. To avoid the effect of sample heterogeneity, the reaction mixture is kept still without stirring. The NIR light beam is guided to propagate through the solution right above the surface of metal salt. The NIR absorption spectra are acquired at 5-min intervals for a reaction period of 6 h. The related concentrations of quadricyclane and norbornadiene in the temporal evolution are determined with the method of partial least squares. A kinetic model for the pseudo-first-order reaction is derived considering the diffusion motion. Accordingly, the second-order rate constant for the isomerization catalyzed by CuSO4 and SnCl2, respectively, are determined to be (1.38 ?± 0.04) ?? 10-3 and (4.62 ?± 0.09) ?? 10-3 min-1 g-1. The norbornadiene is produced via a one-site coordination between the reactant and the catalyst. The product contribution from the intermediate of a two-site coordination is negligible in our system. The obtained result for CuSO4 is comparable with that detected by using Raman spectroscopy.

Valence Isomerization of Quadricyclene Mediated by Illuminated Semiconductor Powders

Ikezawa, Hideo,Kutal, Charles

, p. 3299 - 3303 (1987)

Quadricyclene undergoes valence isomerization to norbornadiene in the presence of photoexcited n-type semiconductor powders.For samples irradiated under comparable conditions of time and intensity, the yield of the diene product varies with (i) the semiconductor in the order CdS > TiO2 > ZnO and (ii) the solvent in the order dichloromethane > acetonitrile > tetrahydrofuran.The presence of oxygen in a sample diminishes the product yield, whereas both methylviologen dication and diphenylamine enhance the yield.The quantum efficiency of norbornadiene production appearsto be rather low (ca. 10-2 for CdS) in these heterogeneous systems.These observations are interpreted in terms of the redox chemistry that results upon interaction of the photogenerated electron-hole pairs in the semiconductor with the surrounding organic medium.

-

Hogeveen,Nusse

, p. 3667,3668 (1973)

-

Overtone Vibrational Photochemistry of Quadricyclane

Lishan, David G.,Reddy, K. V.,Hammond, George S.,Leonard, Jack E.

, p. 656 - 660 (1988)

The photochemistry of quadricyclane (Q) was explored by single-photon excitation to high vibrational levels.Spectra of the ν = 4-7 carbon-hydrogen overtones were recorded by using intracavity absorption and photoacoustic detection.These spectra were compared to the infrared fundamental spectrum and assigned.Excitation of the ν = 5 and ν = 6 bands of cyclopropanoid and methylenic hydrogens leads to reaction.At least one intermediate, probably a vibrationally excited form of norbornadiene (N), must be involved because partitioning among various reaction channels is pressure dependent.Apparent rate constants were measured and correlated with variations in pressure according to the Stern-Volmer relationship.Experimental values were compared with rate constants calculated by RRKM theory.Although there is a modest amount of "excess" reaction observed for the lowest excitation energies above threshold, overall evaluation provides no significant evidence for concentration of energy in localized modes for times that are long compared with reaction times.

Kinetics of the Isomerization of Quadricyclane to Norbornadiene Promoted by Tin(II) Chloride and Palladium(II) Chloride

Patrick, Timothy B.,Bechtold, Dana S.

, p. 1935 - 1937 (1984)

The conversion of quadricyclane to norbornadiene is promoted by both SnCl2 and PdCl2.The SnCl2 reaction occurs by a second-order process with activation parameters of ΔG(excit.), ΔH(excit.), and ΔS(excit.) of 22.5 kcal/mol, 13.9 kcal/mol, and -28.7 eu, respectively.The PdCl2-promoted reaction occurs by formation of an equilibrium species and follows Michaelis-Menton kinetics.A theoretical interpretation based on the Dewar-Duncanson model of bonding of metal ions with olefins is used to describe possible mechanistic differences in the reactions.

Triplex Promoted Intersystem Crossing of Ion-Radical pairs in the Photosensitized Valence Isomerization of Quadricyclane: Chemically Induced Dynamic Nuclear Polarization (CIDNP) Evidence

Yang, Li,Zhang, Mao-Xi,Liu, You-Cheng,Liu, Zhong-Li,Chow, Yuan L.

, p. 1055 - 1056 (1995)

Photosensitized valence isomerization of quadricyclane to norbornadiene by dibenzoylmethanatoboron difluoride in the presence of durene shows a CIDNP effect which is opposite in direction to that occurring in the absence of durene, demonstrating possible participation of triplexes in the durene co-sensitized reaction.

Reactions of Quadricyclane with Sulphur Dioxide: Formation of a Stable β-Sultine and Catalysed Isomerization to Norbornadiene

Lucchi, Ottorino De,Lucchini, Vittorio

, p. 464 - 465 (1982)

Sulphur dioxide, as solvent or in chloroform, catalyses the isomerization of quadricyclane (1) to norbornadiene and cycloadds to (1) to afford exo-3-oxa-4-thiatricyclo2,5>non-7-ene 4-oxide (3); in the presence of a deficiency of sulphur dioxide, (3) is remarkably stable in solution, but decomposes rapidly as pure product.

-

Frey

, p. 365 (1964)

-

Rhodium(I) complexes of the conformationally rigid IBioxMe4 ligand: Preparation of mono-, bis-, and tris-ligated NHC complexes

Chaplin, Adrian B.

, p. 3069 - 3077 (2014)

The preparation and characterization of a series of mono-, bis-, and tris-ligated rhodium(I) complexes of Glorius' conformationally rigid bioxazoline-derived N-heterocyclic carbene ligand IBioxMe4 are described. Through reaction of [Rh(COE)2Cl]2 (COE = cis-cyclooctene) with isolated IBioxMe4, [Rh(IBioxMe 4)(COE)Cl]2 (1), trans-[Rh(IBioxMe4) 2(COE)Cl] (2), and [Rh(IBioxMe4)3Cl] (3) were each isolated by careful choice of the reaction conditions. Further substitution and salt metathesis reactions of 1-3 were investigated, and derivatives containing CO, norbornadiene, and cyclopentadienyl ancillary ligands were readily isolated. Notably, halide abstraction from 2 and 3 using Na[BAr F4] (ArF = 3,5-C6H 3(CF3)2) resulted in the formation of low-coordinate T-shaped cis-[Rh(IBioxMe4)2(COE)][BAr F4] (9) and [Rh(IBioxMe4)3][BAr F4] (11). The solid-state structures of 2, 9, and 11 each feature IBioxMe4 ligands that bind unusually with tilted coordination geometries.

Alumina-Anchored Cobalt Porphine Catalysts for the Conversion of Quadricyclane to Norbornadiene

Miki, Sadao,Asako, Yoshinobu,Morimoto, Masayoshi,Ohno, Toshinobu,Yoshida, Zen-ichi,et al.

, p. 973 - 982 (1988)

Methods are described for the preparation of cobalt(II) deuteroporphyrin and cobalt(II) tetrakis(p-sulfonatophenyl)porphine anchored on alumina beads coated with polyaminesulfone-A.Wavelength dispersive X-ray microanalysis showed that the cobalt(II) porphine distributes within the catalyst outer surface layer of ca. 100 μm depth.The catalysts are highly active for the cycloreversion of quadricyclane to norbornadiene.A detailed kinetics of the isomerization using an isothermal recycle reactor gave a rate expression of Langmuir-Hinshelwood type.The catalysts gradually lose their activity, which can be regenerated completely by heating the catalysts at 200 deg C in vacuo.

-

Walsh,Wells

, p. 149,150, 151 (1975)

-

-

Herndon,Lowry

, p. 1922 (1964)

-

Thermal Decomposition of a Series of 1,2-Diazetines

Breton, Gary W.,Shugart, John H.

, p. 8643 - 8649 (2003)

A homologous series of tricyclic diazetines (6a-c), differing by the number of methylene groups in the saturated bridges of the fused carbon bicycles, was synthesized. The ΔH? of decomposition for each of the diazetines to afford N2 and the corresponding alkene was determined experimentally: 6a, 31.7; 6b, 39.3; 6c, 38.8 kcal/mol. The ground-state strain energy of each diazetine was estimated utilizing computationally obtained ΔHf's for each of the experimentally investigated diazetines as well as several other diazetines whose ΔH?'s had been previously reported in the literature. The sum of the ground-state strain energies and ΔH?'s of decomposition for all of the diazetines was nearly constant, with an average value of 59 kcal/mol, suggesting that all of the diazetines decompose via the same mechanism. Generally, the higher the ground-state strain energy of the diazetine, the less the ΔH? for decomposition. The decomposition transition states for 6a-c and 7 were modeled computationally at the RB3LYP/6-311+G(3df,2p)//UB3LYP/6-31+G(d,p) level. The agreement of the experimentally determined ΔH? values with transition-state energies obtained computationally supports the reaction mechanism originally proposed by Yamabe that the elimination process occurs by an unsymmetrical, yet concerted, transition state with strong biradical character.

Cycloreversion of Quadricyclane to Norbornadiene Catalyzed by Tin (II) Complexes

Landis, M.E.,Gremaud, D.,Patrick, T.B.

, p. 375 - 378 (1982)

The conversion of quadricyclane (1) to norbornadiene (2) is catalyzed by stannous chloride and stannous chloride-phosphine complexes.A newly synthesized polymer-bound phosphine-stannous chloride complex also proved effective in the catalytic conversion 1 to 2.

Abel, E. W.,Bennet, M. A.,Wilkinson, G.

, (1959)

-

Murov et al.

, p. 2957 (1968)

-

PHOTOINDUCED ADDITION OF NUCLEOPHILES TO BICYCLOHEPTA-2,5-DIENE

Gassman, Paul G.,Olson, Kurt D.

, p. 19 - 22 (1983)

The 1-cyanonaphthalene photosensitized addition of water and methanol to the cation-radical of bicyclohepta-2,5-diene is described.

REDOX-AUXILIARY CATALYSIS

-

Paragraph 0007; 0101, (2015/05/26)

Disclosed herein is a method of activating a compound for a chemical reaction comprising functionalizing a compound with a redox auxiliary group and oxidizing the redox auxiliary group that is bonded to the compound, thereby activating the compound, wherein the activated compound undergoes a chemical reaction to form a product and the oxidation of the redox auxiliary group is reversible. Methods of making and using these materials are also disclosed.

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