אסיף מאגר המחקר החקלאי

Cleavage of the epoxide ring in trans-epoxy-alcohols by sodium borohydride in methanol

Year:

1978

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Weissenberg, M., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, Israel
Krinsky, P., Faculty of Agriculture, Hebrew University of Jerusalem, P.O. Box 12, Rehovot 76-100, Israel
Glotter, E., Faculty of Agriculture, Hebrew University of Jerusalem, P.O. Box 12, Rehovot 76-100, Israel

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Abstract:

The epoxide ring in steroidal trans-αβ and βy-epoxy-alcohols is cleaved by sodium borohydride in refluxing methanol to give the corresponding methoxyhydrins, in contrast to the cis-epoxy-alcohols which remain unchanged. The steric requirements of the reaction and a mechanism involving the intermediate formation of a boron complex with the substrate are discussed.

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