24054-29-3Relevant academic research and scientific papers
Evidence for 2-Hexene-1,6-diyl Diradicals Accompanying the Concerted Diels-Alder Cycloaddition of Acrylonitrile with Nonpolar 1,3-Dienes
Li, Yufei,Padias, Anne Buyle,Hall, H. K.
, p. 7049 - 7058 (2007/10/02)
The spontaneous reactions of a series of alkyl 1,3-dienes with acrylonitrile (AN) were investigated.Reproducible spontaneous copolymerizations were shown to compete with the expected concerted cycloadditions.For dienes which exist in s-cis/s-trans equilibrium, both copolymer and cycloadduct are formed.Kinetic measurements show that the alternating copolymerization and cycloaddition are two independent paralell second order reactions.With 1,3-cyclohexadiene and 1,2-dimethylenecyclohexane, for which s-gauche is in equilibrium with s-cis, copolymerization still competes with cycloaddition.The s-trans-locked verbenene forms only copolymer, while s-cis-locked cyclopentadiene and 1,2-dimethylenecyclopentane form only cycloadduct rapidly.Our explanation involves a 2-hexene-1,6-diradical, formed by combination between the terminal carbons of the s-gauche or s-trans diene and acrylonitrile.This does not cyclize but initiates copolymerization.Competitively s-cis conformer undergoes classical concerted addition.
Natuerlich vorkommende Terpen-Derivate, 306. Synthese eines Furansesquiterpens aus Eumorphia prostata
Bohlmann, Ferdinand,Fiedler, Lothar
, p. 227 - 231 (2007/10/02)
Starting with 5-methyl-2-cyclohexen-1-one (1) through the intermediate 4 the cyclopentene carbaldehydes 5 and 6 were synthesized.Wittig reaction led to epimeric nitriles 7 and 8, which after conversion to the aldehydes 9 and 10 on reaction with β-furyllit
