J. Weber, U. Brinker
Nov 18, 1996
Citations
0
Influential Citations
6
Citations
Journal
Tetrahedron
Abstract
Abstract 1-Bromo-5-bromomethyl-6,6-dichlorobicyclo[3.1.0]hexane (9) was treated with alkyllithium at different temperatures. After halogen metal exchange in 9, two competing 1,n-elimination reactions take place. A 1,2-elimination of organolithium compound 12 leads to strained 1,3-bridged cyclopropene 10 which undergoes a cyclopropene-vinylcarbene rearrangement to 17. Insertion of 17 into the ether solvent affords isomers 18a and 18b. In contrast, 1,4-eliminations of organolithium compound 13 generate butadienes 14 and 16, respectively. The formation of the products is temperature dependent.