Tetrahedron

2-Tosyloxymethylcyclanones: Ring size dependence of fragmentation versus intramolecular alkylation

U Heinz, E Adams, R Klintz, P Welzel

Index: Heinz, Uwe; Adams, Elisabeth; Klintz, Ralf; Welzel, Peter Tetrahedron, 1990 , vol. 46, # 12 p. 4217 - 4230

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Citation Number: 5

Abstract

The results reported seem to indicate, that in the presence o: a nucleophilic base intramolecular alkylation is the normal reaction mode of tosyloxymethylcyclanones of type 14 and that the fragmentation reaction of five-membered compounds is the exception, probably because of the high steric energy of the alkylation transition states, eg of type E.