SYNTHESIS OF INDENONE BY SELF-CONDENSATION OF 1-ACETYL-2-METHYLCYCLOPENTENE AND SUBSEQUENT UNUSUAL AUTOXIDATION

Authors
MILOUDI A ELABED D PONS JM SANTELLI M
Citation
A. Miloudi et al., SYNTHESIS OF INDENONE BY SELF-CONDENSATION OF 1-ACETYL-2-METHYLCYCLOPENTENE AND SUBSEQUENT UNUSUAL AUTOXIDATION, Tetrahedron, 52(29), 1996, pp. 9785-9792
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
29
Year of publication
1996
Pages
9785 - 9792
Database
ISI
SICI code
0040-4020(1996)52:29<9785:SOIBSO>2.0.ZU;2-X
Abstract
Potassium tert-butoxide induced self-condensation of 1-acetyl-2-methyl -cyclopentene leads to -methylcyclopent-1'-enyl)bicyclo[4.3.0]non-3-en -2- one 2 in 35% yield when one equivalent of dimethyl sulfate is adde d. Dienone 2 undergoes facile autoxidation leading to the correspondin g epoxide 12 and triketone 13. Copyright (C) 1995 Elsevier Science Ltd .