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Mechanistic insights into the opening of epoxides with trimethylsilyl cyanide - zinc iodide

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
27
Issue
52
Identifiers
DOI: 10.1016/s0040-4039(00)87794-1

Abstract

Abstract endo -2,3-Epoxy-1,7,7-trimethylbicyclo[2.2.1]heptane reacted with trimethylsilyl cyanide in the presence of zinc iodide to produce a complex mixture of products. The major product, anti -7-trimethylsiloxy- endo -2,3,3-trimethyl- exo -2-isocyanobicyclo[2.2.1]heptane was obtained in 72% yield. In addition, eight other products were identified in yields ranging from 10% to 1%. All of the products could be rationalized on the basis of initial generation of a carbocationic intermediate.

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