Cleavage of cyclopropyl ketones mediated by alkyl mercury(II)

DI CHENNA PABLO H.; FERRARA, A.; GHINI, ALBERTO A.; BURTON, GERARDO

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1

RSC publishing

Año: 2002 vol. 2 p. 227 - 231

0300-922X

Cyclopropyl ketones are converted into their hydrazones which react with mercury(ǼǼ) oxide and mercury(ǼǼ) acetate to give £-(acetoxymercurio)alkyl acetates. These are reduced in situ to the corresponding £-acetoxyalkylmercury(ǼǼ) hydrides which rearrange spontaneously with cleavage of the cyclopropane ring. The procedure is used to obtain Dhomo- and 17(13 18)-abeo-pregnanes.ǼǼ) oxide and mercury(ǼǼ) acetate to give £-(acetoxymercurio)alkyl acetates. These are reduced in situ to the corresponding £-acetoxyalkylmercury(ǼǼ) hydrides which rearrange spontaneously with cleavage of the cyclopropane ring. The procedure is used to obtain Dhomo- and 17(13 18)-abeo-pregnanes.