Tetrahedron Letters p. 1405 - 1408 (1982)
Update date:2022-07-30
Topics:
Cairns, Peter M.
Crombie, Leslie
Pattenden, Gerald
The additions of thiophenol to alkenylidenecyclopropanes (e.g. 3, 14) are found to be highly regioselective and stereoselective leading to endo- (or cis-) vinyl sulphide adducts (e.g. 4, 15) resulting from additions to the 1,4-double bonds in the starting materials.Thiophenol addition to (1) leads to a mixture of the vinyl sulphides (16) and (17) which undergo Cope rearrangement producing the cycloheptadiene (18); hydrolysis of (18) then gives karahanaenone (19) an odoriferous constituent of Japanese hop and Cypress oil.
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Doi:10.1016/S0040-4039(00)81536-1
(1983)Doi:10.1016/j.bmcl.2007.09.088
(2007)Doi:10.1107/S0108270102012386
(2002)Doi:10.1016/j.tetasy.2009.02.039
(2009)Doi:10.1021/jo0507892
(2005)Doi:10.1021/jo00167a013
(1983)
