The Journal of Organic Chemistry

Solvomercuration-demercuration. 8. Oxymercuration-demercuration of methoxy-, hydroxy-. and acetoxy-substituted alkenes

HC Brown, GJ Lynch

Index: Brown, Herbert C.; Lynch, Gary J. Journal of Organic Chemistry, 1981 , vol. 46, # 3 p. 531 - 538

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Citation Number: 33

Abstract

The oxymercuration-demercuration (OM-DM) of a series of methoxy-, hydroxy-, and acetoxy- substituted alkenes was examined. The systems examined were the allyl, crotyl, 3-buten-l-yl, 4-penten-l-yl, and 5-hexen-1-yl. The methoxyalkenes undergo hydration with very high regioselectivity and almost quantitative yield in all cases. However, a small-I effect is observed in the case of the allylalkene (97.1% Markovnikov vs. 99.5% in 1-hexene). ...