The Journal of Organic Chemistry

Solvomercuration-demercuration. 9. Oxymercuration-demercuration of chloro-, epoxy-, and thiomethyl-substituted alkenes

HC Brown, GJ Lynch

Index: Brown, Herbert C.; Lynch, Gary J. Journal of Organic Chemistry, 1981 , vol. 46, # 5 p. 930 - 939

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Citation Number: 20

Abstract

The oxymercuration-demercuration (OM-DM) of allyl, crotyl, 3-buten-l-yl, 4-penten-l-yl, and 5- hexen-1-yl chlorides and methyl sulfides as well as 3, 4-epoxy-l-butene, 4, 5-epoxy-l- pentene, and 5, 6-epoxy-l-hexene has been studied. Allyl chloride undergoes a slow but normal OM to give the Markovnikov oxymercurial. However, in situ demercuration under the standard conditions (NaOH, NaBH,) gives only allyl alcohol. Fortunately, demercuration ...