73679-39-7

Basic information

• Product Name: (1β,3α,6α,8β)-Tetracyclo[6.2.1.13,6.02,7]dodeca-2(7)-ene
• Synonyms: (1β,3α,6α,8β)-Tetracyclo[6.2.1.13,6.02,7]dodeca-2(7)-ene;1,2,3,4,5,6,7,8-Octahydro-1α,4α:5β,8β-dimethanonaphthalene;1,2,3,4,5,6,7,8-Octahydro-1β,4β:5α,8α-dimethanonaphthalene;anti-Sesquinorbornene;1,4:5,8-Dimethano-4A,8A-(methanoxymethano)naphthalene-9,11-dione, octahydro-(1alpha,4alpha,4abeta,5beta,8alpha,8abeta)-
• CAS NO: 73679-39-7
• Molecular Formula: C₁₂H₁₆
• Molecular Weight: 160.26
• Mol File: 73679-39-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 246.1°C at 760 mmHg
• Flash Point: 80°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 0.0433mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: (1β,3α,6α,8β)-Tetracyclo[6.2.1.13,6.02,7]dodeca-2(7)-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1β,3α,6α,8β)-Tetracyclo[6.2.1.13,6.02,7]dodeca-2(7)-ene(73679-39-7)
• EPA Substance Registry System: (1β,3α,6α,8β)-Tetracyclo[6.2.1.13,6.02,7]dodeca-2(7)-ene(73679-39-7)

Safety Data

• Hazardous Substances Data: 73679-39-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H16/c1-2-8-5-7(1)11-9-3-4-10(6-9)12(8)11/h7-10H,1-6H2

Upstream product

• 97806-44-5 anti-sesquinorbornatriene 
• 89746-15-6 C₁₃H₁₆O₂ 
• 108587-04-8 C₁₄H₁₆N₂ 
• 89726-59-0 4a-chloro-1,2,3,4,4a,5,6,7,8,8a-decahydro-1,4:5,8-exo,endo-dimethanonaphthalene 
• 73654-77-0 1,2,3,4,4a,5,6,7,8,8a-decahydro-1,4,5,8-exo,endo-dimethanonaphthalene-4a,8a-dicarboxylic acid 
• 92989-52-1 1,2,3,4,4a,5,6,7,8,8a-decahydro-8a-hydroxy-1,4:5,8-exo,endo-dimethanonaphthalene-4a-carboxylic acid 
• 68841-81-6 anti-sesquinorbornadiene 
• 6295-85-8 (+/-)-norbornane-dicarbonitrile-(2endo.3exo) 
• 6343-16-4 bicyclo<2.2.1>hept-5,6-ene-2α,3β-dicarbonitrile 
• 825-24-1 bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarbonitrile 
• 73654-76-9 1,2,3,4,4a,5,8,8a-octahydro-1,4,5,8-exo,endo-dimethanonaphthalene-4a,8a-dicarboxylic acid 
• 19479-86-8 bicyclo<2.2.1>hept-2-ene-2,3-dicarboxylic anhydride 
• 16508-04-6 bicyclo<2,2,1>hept-2-ene-2,3-dicarboxylic acid 
• 825-24-1 2,3-dicyanonorbornadiene 

Downstream Products

• 15914-95-1 exo-endo-tetracyclo<6.2.1.1^3,6.0^2,7>dodecane 
• 79692-83-4 C₁₅H₂₂O 
• 73654-78-1 anti-1,2,3,4,5,6,7,8-octahydro-1,4,5,8-exo,endo-dimethanonaphthalene-4a,8a-epoxide 
• 15914-95-1 C₁₂H₁₈ 

Relevant articles and documents

EXPERIMENTAL EVIDENCE ESTABLISHING AN UPPER LIMIT TO THE ACTIVATION BARRIER FOR THE BUTTERFLY BENDING OF THE DOUBLE BOND IN ANTI-SESQUINORBORNENE

Low temperature 13C NMR and theoretical results are presented which imply that in the groundstate of anti-sesquinorbornene the double bond is either pyramidal with a very low barrier to inversion or planar.

SYNTHESIS OF anti-SESQUINORBORNENE AND RELATED POLYCYCLIC ALKENES via REDUCTIVE ELIMINATION OF VICINAL DICYANO DERIVATIVES

A methodology for the preparation of both endocyclic unsaturated molecules via reductive elimination of vicinal dicyano derivatives is reported.The method is useful for the preparation of anti-sesquinorbornene and related hitherto unknown molecules starting from the respective vicinal dicyano derivatives which are readily available via Diels-Alder reactions.From a practical point of view, the best decyanation procedure for these substrates is to use finely dispersed sodium in tetrahydrofuran under sonication.The X-ray analysis of anti-1,4,4a,5,8,8a-hexahydro-1,4;5,8-dimethanonaphthalene-4a,8a-dicarbonitrile, 3, is reported.Crystal data: orthorhombic, space group P212121; Z=4; a=16.059(5), b=8.920(3), c=7.592(3) Angstroem; V=1087.5 Angstroem3, Dc=1.27 g*cm-3.

Improved synthesis of anti-sesquinorbornene

Treatment of methyl hydrogen decahydro-1,4:5,8-exo,endo-dimethanonaphthalene-4a,8a-dicarboxylate with lead tetraacetate in benzene-acetic acid replaces the carboxyl group by an acetoxy group.Hydrolysis of this product with 25percent sulfuric acid at 130 deg C forms 8a-hydroxydecahydro-1,4:5,8-exo,endo-dimethanonaphthalene-4a-carboxylic acid 10.The reaction between 10 and benzenesulfonyl chloride in pyridine containing triethylamine at 95 deg C produces anti-sesquinorbornene 1 in 34percent yield.In the absence of triethylamine 1 is converted to the hydrochloride.The iodohydroperoxide of 1 is converted by silver acetate at 0 deg C to the diketone in a luminescent reaction.The 1,2-dioxetane could not be isolated.Decahydro-1,4:5,8-exo,exo-dimethanonaphthalene-4a,8a-dicarboxylic anhydride is converted slowly by methoxide ion in methanol at 150 deg C to the monomethyl ester which then undergoes demethylation.The isomeric exo,endo anhydride undergoes reaction readily with methoxide ion at 80 deg C.