A cobaloxime-mediated radical route to butenolides

Bruce Branchaud, Rachel M. Slade, Samantha K. Janisse

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Photolysis of alkyl cobaloximes with maleic anhydride and PhSSPh proceeds via radical alkene addition and subsequent PhSSPh trapping. The product trans 3-phenylthio 4-alkyl succinic anhydrides can be converted by oxidation and thermal syn elimination into 3-substituted maleic anhydrides, which are known to be regioselectively and chemoselectively reduced to produce γ-hydroxybutenolides or butenolides.

Original languageEnglish (US)
Pages (from-to)7885-7888
Number of pages4
JournalTetrahedron Letters
Volume34
Issue number49
DOIs
StatePublished - Dec 3 1993
Externally publishedYes

Fingerprint

Maleic Anhydrides
Succinic Anhydrides
Photolysis
Alkenes
Hot Temperature
Oxidation
cobaloxime

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

A cobaloxime-mediated radical route to butenolides. / Branchaud, Bruce; Slade, Rachel M.; Janisse, Samantha K.

In: Tetrahedron Letters, Vol. 34, No. 49, 03.12.1993, p. 7885-7888.

Research output: Contribution to journalArticle

Branchaud, Bruce ; Slade, Rachel M. ; Janisse, Samantha K. / A cobaloxime-mediated radical route to butenolides. In: Tetrahedron Letters. 1993 ; Vol. 34, No. 49. pp. 7885-7888.
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