3008-14-8

Basic information

• Product Name: Bicyclo(2.2.2)oct-5-ene-2-carbonitrile, (1alpha,2alpha,4alpha)-
• Synonyms: Bicyclo(2.2.2)oct-5-ene-2-carbonitrile, (1alpha,2alpha,4alpha)-
• CAS NO: 3008-14-8
• Molecular Formula: C9H11N
• Molecular Weight: 133.19034
• Mol File: 3008-14-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 244.6°C at 760 mmHg
• Flash Point: 85.9°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 0.03mmHg at 25°C
• Refractive Index: 1.523
• CAS DataBase Reference: Bicyclo(2.2.2)oct-5-ene-2-carbonitrile, (1alpha,2alpha,4alpha)-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo(2.2.2)oct-5-ene-2-carbonitrile, (1alpha,2alpha,4alpha)-(3008-14-8)
• EPA Substance Registry System: Bicyclo(2.2.2)oct-5-ene-2-carbonitrile, (1alpha,2alpha,4alpha)-(3008-14-8)

Safety Data

• Hazardous Substances Data: 3008-14-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H11N/c10-6-9-5-7-1-3-8(9)4-2-7/h1,3,7-9H,2,4-5H2

Upstream product

• 94991-41-0 (+/-)-bicyclo[2.2.2]oct-5-ene-2endo-carboxamide 
• 1165952-91-9 cyclohexa-1,3-diene 
• 107-13-1 acrylonitrile 
• 50845-86-8 bicyclo[2.2.2]oct-5-ene-2-carbonyl chloride 
• 94991-41-0 bicyclo<2.2.2>oct-5-ene-2-exo-carboxamide 
• 20507-56-6 bicyclo<2.2.2>oct-5-ene-2-exo-carboxylic acid 

Downstream Products

• 20507-56-6 (2-endo)-bicyclo<2.2.2>oct-5-ene-2-carboxylic acid 

Relevant articles and documents

Orbital unsymmetrization of olefins arising from non-equivalent orbital interactions. σ-π Coupling in bicyclo[2.2.2]octenes

We characterized experimentally the substituent effect of a 5-exo substituent on the π facial selectivities of bicyclo[2.2.2]octenes toward electrophilic oxidative reactions such as epoxidation and dihydroxylation, and we discuss the underlying orbital interactions of vicinal σ orbitals and the olefinic π orbital involved in bicyclo[2.2.2]octenes, and commonly in methylenenorbornanes. Of significance is the out-of-phase motif of these σ- π couplings. Electron-withdrawing substituents such as cyano and carboxylic acid groups unequalize the relevant σ-π coupling, leading to the observed syn-facial preference. Alkyl substituents exhibit an electron-donative perturbing effect, depending on the bicyclic ring system.

THE INFLUENCE OF CAPTODATIVE EFFECT ON THE DIENOPHILICITY OF OLEFINS. THE EASY DIELS-ALDER REACTION OF α-METHYLTHIOACRYLONITRILE WITH CYCLOHEXADIENE

We show that the cycloaddition of α-methylthioacrylonitrile to cyclohexadiene is faster than that of acrylonitrile.This indicates that the captodative substitution exerts an accelerating effect on the Diels-Alder reaction despite the larger steric bulk of the methylthio group compared to hydrogen.

216. Bicyclooctanes. Syntheses and Hydrolyses of 6-exo-substituted 2-exo- and 2-endo-Bicyclooctyl p-Toluenesulfonates. Part 9

The synthesis of the title compounds and their hydrolysis products in 70percent dioxane are described.