Preparation of cyclic ethers via a transacetalization-cationic cyclization sequence

…, CPD Longford, NT Lane, DW Thompson

Index: Nikolic, Nikola A.; Gonda, Elizabeth; Longford, C. P. Desmond; Lane, Nancy T.; Thompson, David W. Journal of Organic Chemistry, 1989 , vol. 54, # 11 p. 2748 - 2751

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Citation Number: 23

Abstract

Conclusions The observed kinetics require that the mechanism of the osmium tetraoxide catalyzed reactions of a-pinene and cyclohexene with trimethylamine N-oxide involve oxidation of a relatively substitution-inert osmium (V1) ester to a substitution-labile osmium (VII1) species in the rate-determining step. Reaction of osmium (VII1) with the alkene to form osmium (V1) ester must be rapid. The observation that the trimethylamine N-oxide directly ...