W. Bailey, A. Khanolkar
Sep 9, 1991
Citations
0
Influential Citations
20
Citations
Journal
Tetrahedron
Abstract
Abstract The naturally occurring sesquiterpene (±)-cuparene [1,1,2-trimethyl-2-(4-methylphenyl)cyclopentane], which contains two contiguous quaternary centers, is produced in good yield by 5-exo-trig cyclization of the 5-hexenyllithium ( 2 ) generated from 6-iodo-3,3-dimethyl-2-(4-methylphenyl)-1-hexene ( 3 ) by low temperature lithium - iodine exchange. In contrast, radical mediated cyclization of 3 proceeds via the 6-endotrig mode to give 1,1-dimethyl-2-(4-methylphenyl)cyclohexane.