Journal of Organic Chemistry p. 3707 - 3712 (1982)
Update date:2022-08-29
Topics:
Bach, Robert D.
Woodard, Robert A.
Anderson, Thomas J.
Glick, Milton D.
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)-α-acetoxy-β-(acetoxymercuri)stilbene by a suprafacial addition of Hg(OAc)2.A simple method for the in situ acetoxymercuration-demercuration of dialkyl-substituted alkynes to afford vinyl acetates is described.The sodium borohydride reduction of vinyl mercurials was shown to produce divinyl mercurials while demercuration with zinc dust in acetic acid provided a useful method for the preparation of vinyl acetates.
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