Tetrahedron p. 14641 - 14650 (1996)
Update date:2022-08-11
Topics:
Weber, Juergen
Brinker, Udo H.
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.
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