The formation of catenanes. The mobius strip approach revisited.

G.J.M. Gruter, O.S. Akkerman, F. Bickelhaupt

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

The "Möbius strip approach" for the synthesis of catenanes requires that a ladder shaped molecule (doubly functionalized at both ends) twists twice prior to bimacrocyclization. A successful application of this strategy was claimed in the 1960's. However, the catenanes were believed to be formed via a Möbius strip mechanism since, at that time, a metal coordinated all carbon cyclobutane was assumed to be an intermediate in the olefin metathesis. Although the incompatibility of the Möbius strip mechanism and the (later proposed) actual metathesis mechanism has been pointed out, the original claim keeps being cited as a successful one even in the recent literature. In this paper, the background of this mechanistic misconception is discussed, and it is demonstrated that the formation of catenanes in olefin metathesis is resulting from a statistical threading process.
Original languageEnglish
Pages (from-to)2565-2572
JournalTetrahedron Symposia-in-Print
Volume52
DOIs
Publication statusPublished - 1996

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