Structure and reactivity. I. Deuteration of substituted cyclohexenes: stereoselectivity of addition and exchange in the homoallylic position

Journal Article · Fri Apr 01 04:00:00 EST 1977 · J. Catal.; (United States)

DOI:https://doi.org/10.1016/0021-9517(77)90159-2· OSTI ID:7260347

Aycard, J P; Bodot, H

A series of substituted and deuterium labeled cyclohexenes were deuterated on a Pd/C catalyst, and the products were analyzed by NMR spectroscopy. The compounds were: methyl-2,2,5,5-tetradeuterio-3,4-dimethyl-3-cyclohexenecarboxylate, methyl-2,2,5,5-tetradeuterio-4-t-butyl-3-cyclohexenecarboxylate, cis- and trans-2,5,5-trideuterio-2-alkyl-3-cyclohexenecarboxylic acid methyl ester or nitrile (alkyl being methyl or t-butyl). The cis isomers underwent exclusive addition on their least hindered side and a stereospecific exchange of the hydrogen located in a trans vicinal position with respect to the carboxyl or the cyano groups was noted. This feature was absent for most of the trans isomers. The exchange and addition mechanisms are discussed.

• Research Organization: Univ. de Provence, Marseille
• OSTI ID: 7260347
• Journal Information: J. Catal.; (United States), Journal Name: J. Catal.; (United States) Vol. 47:1; ISSN JCTLA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400303* -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
ADSORBENTS
ALKENES
CATALYTIC EFFECTS
CHARCOAL
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CYCLOALKENES
DEUTERATION
ELECTRONIC STRUCTURE
ELEMENTS
HYDROCARBONS
KINETICS
MAGNETIC RESONANCE
METALS
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
PALLADIUM
PLATINUM METALS
REACTION KINETICS
RESONANCE
STEREOCHEMISTRY
TRANSITION ELEMENTS