Issue 2, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Cleavage of cyclopropylketones mediated by alkylmercury(ii) hydrides†‡

Pablo H. Di Chenna,a   Andrés Ferrara,a   Alberto A. Ghinia  and  Gerardo Burton*a  

* Corresponding authors

a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EHA Buenos Aires, Argentina
E-mail: burton@qo.fcen.uba.ar
Fax: 54-11-4576-3385

Abstract

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

Graphical abstract: Cleavage of cyclopropyl ketones mediated by alkylmercury(ii) hydrides

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Article information

DOI
https://doi.org/10.1039/B107258G
Article type
Paper
Submitted
10 Aug 2001
Accepted
22 Nov 2001
First published
18 Dec 2001

J. Chem. Soc., Perkin Trans. 1, 2002, 227-231

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Cleavage of cyclopropyl ketones mediated by alkylmercury(II) hydrides

P. H. Di Chenna, A. Ferrara, A. A. Ghini and G. Burton, J. Chem. Soc., Perkin Trans. 1, 2002, 227 DOI: 10.1039/B107258G

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