Jr. Hanson et al., NEIGHBORING GROUP PARTICIPATION IN THE TETRACYANOETHYLENE CATALYZED METHANOLYSIS OF SOME STEROIDAL HYDROXY-EPOXIDES, Journal of chemical research. Synopses (Print), (6), 1998, pp. 300
An adjacent cis 5-hydroxy group changes the regio- and stereo-chemistr
y of the TCNE-catalysed methanolysis of steroidal 3,4-epoxides from tr
ans diaxial to diequatorial cleavage; the stereochemistry of the two p
roducts is established by X-ray crystallography.