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Simmons‐Smith reaction of allylic hydroxylated long chain α, β‐unsaturated esters
Author(s) -
Ahmad M. S.,
Osman S. M.
Publication year - 1980
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02662060
Subject(s) - cyclopropanation , diiodomethane , allylic rearrangement , chemistry , yield (engineering) , reagent , ether , medicinal chemistry , zinc , organic chemistry , catalysis , materials science , surface energy , metallurgy
Abstract The reaction of methyl 4‐hydroxy‐ trans ‐2‐hexadecenoate [1 b ] with diiodomethane in the presence of zinc‐copper couple yielded methyl 4‐methoxy‐ trans ‐2,3‐methylenehexadecanoate [2] in a 70% yield, together with methyl 4‐hydroxy‐ trans ‐2,3‐methylenehexadecanoate [3] (∼20%). The presence of an allylic hydroxyl group in the α,β‐unsaturated ester increases the yield of the cyclopropanation product. The formation of o ‐methyl ether reveals the dual role of cyclopropanation and etherification by S.S. reagent of a hydroxylated olefinic compound.