Effect of conformation and stereochemistry in substitution reactions of fused chlorocyclobutanones: oxyallyl cation intermediates

Alfred Hassner, John L. Dillon, Larry R. Krepski, Kay D. Onan

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

Fused α-acyloxycyclobutanones, whose conformation and stereochemistry have been unambiguously established by X-ray analysis, undergo an unusual displacement with methoxide as nucleophile to produce α-methoxycyclobutanones. The success of this reaction, which suggests the intermediacy of an oxyallyl cation, is highly dependent on conformational and steric factors.

Original languageEnglish
Pages (from-to)1135-1138
Number of pages4
JournalTetrahedron Letters
Volume24
Issue number11
DOIs
StatePublished - 1983
Externally publishedYes

Bibliographical note

Funding Information:
This research was supported by the DHEW Grant CA-19203 from the NC1 and a

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