Neighbouring Group Participation in the Tetracyanoethylene Catalysed Methanolysis of some Steroidal Hydroxy-epoxides

Abstract

An adjacent cis 5-hydroxy group changes the regio- and stereo-chemistry of the TCNE-catalysed methanolysis of steroidal 3,4-epoxides from trans diaxial to diequatorial cleavage; the stereochemistry of the two products is established by X-ray crystallography.

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