Rearrangements of norbornenyl radicals: Further evidence as to the mechanism of borohydride reduction of organomercurials

V. M.A. Chambers, W. R. Jackson, G. W. Young

Research output: Contribution to journalArticleResearchpeer-review

16 Citations (Scopus)

Abstract

Reductions of 3-acetoxy-5-norbornen-2-yl mercuric chloride, 5-acetoxy-3-nortricyclyl mercuric chloride, and 7-anti-acetoxy-2-exo- bromonorborn-5-ene with tributyltin hydride, triphenyltin hydride, or photochemically in methanol give similar isomeric mixtures of 2-exo-acetoxynorbornene, 7-anti-acetoxynorbornene, and 3-acetoxynortricyclene, as does reduction of the mercurials with sodium borohydride in aqueous tetrahydrofuran, indicating that a radical mechanism operates in the latter reaction.

Original languageEnglish
Pages (from-to)1275-1276
Number of pages2
JournalJournal of the Chemical Society D: Chemical Communications
Issue number20
DOIs
Publication statusPublished - 1 Jan 1970
Externally publishedYes

Cite this