138100-45-5Relevant academic research and scientific papers
Construction of a Sterically Congested Carbon Framework via 5-Hexenyllithium Cyclization. Synthesis of (+/-)-Cuparene.
Bailey, William F.,Khanolkar, Atmaram D.
, p. 7727 - 7738 (2007/10/02)
The naturally occuring sesquiterpene (+/-)-cuparene , 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-endo-trig mode to give 1,1-dimethyl-2-(4-methylphenyl)cyclohexane.
