Unusual transformations in oxabicyclooctanones. An apparent oxypromoted electrocyclic opening involving fused cyclobutanols

Alfred Hassner, Simha Naidorf-Meir, Hugo E. Gottlieb, Felix Frolow

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Reaction of oxabicyclooctanone 3 with nucleophiles involves not only cine substitution but ring opening to cyclobutenones which are capable of further transformations. With azide as a nucleophile, further reactions occur, among them an oxy-promoted electrocyclic cyclobutane opening, with final formation of 8, the structure of which was verified by X-ray diffraction.

Original languageEnglish
Pages (from-to)5669-5672
Number of pages4
JournalTetrahedron Letters
Volume31
Issue number39
DOIs
StatePublished - 1990

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