Stereochemistry of the acetoxymercuration of alkynes. A synthesis of vinyl acetates

RD Bach, RA Woodard, TJ Anderson…

Index: Bach, Robert D.; Woodard, Robert A.; Anderson, Thomas J.; Glick, Milton D. Journal of Organic Chemistry, 1982 , vol. 47, # 19 p. 3707 - 3712

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Citation Number: 39

Abstract

The stereochemistry of acetoxymercuration of 3-hexyne has been established as antarafacial on the basis of an X-ray crystallographic study. Acetoxymercuration of diphenylacetylene afforded (Z)-cY-acetoxy-8-(acetoxymercuri) stilbene by a suprafacial addition of Hg (OAc)? A simple method for the in situ acetoxymercurationdemercuration of dialkyl-substituted alkynes to afford vinyl acatatea is deacribed. The sodium borohydride ...