Simmons-Smith reaction of allylic hydroxylated long chain α, β-unsaturated esters
摘要：
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.
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DOI：
10.1007/BF02662060
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年份：
1980
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来源期刊
Journal of the American Oil Chemists Society
October 1980
引用走势
1982
被引量：6
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