EXPEDIENT SYNTHESIS OF 17-VINYLESTRA-1,3,5(10)-TRIEN-11-ONES FROM 1,3-BUTADIENE

Authors
OUVRARD P TUBUL A SANTELLI M
Citation
P. Ouvrard et al., EXPEDIENT SYNTHESIS OF 17-VINYLESTRA-1,3,5(10)-TRIEN-11-ONES FROM 1,3-BUTADIENE, Bulletin de la Societe chimique de France, 130(6), 1993, pp. 772-778
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
130
Issue
6
Year of publication
1993
Pages
772 - 778
Database
ISI
SICI code
0037-8968(1993)130:6<772:ESO1F1>2.0.ZU;2-E
Abstract
The TiCl4 mediated dialkylation of 4-nitrobutan-2-one ethyleneketal or 5-nitropentan-2-one ethyleneketal by 1,8-bis(trimethylsilyl)octa-2,6- diene led to 1-(2-nitroethyl)-1-methyl-2,5-divinylcyclopentane or -(3- nitropropyl)-1-methyl-2,5-divinylcyclopentane. From these compounds, 1 -methyl-2,5-divinylcyclopentane acetaldehyde or propanal were obtained . 1,3-Dihydrobenzo[c]thiophene 2,2-dioxide carbanion derivative additi on to these aldehydes, oxidation to ketones and heating gives rise to 17-vinylestra-1,3,5(10)-trien-11-ones and 17-vinyl-C-homoestra-1,3,5(1 0)-trien-11-ones.