REGIOSELECTIVE ACETALIZATION OF ESTRA-4.9 -DIENE-3.17-DIONE - INVESTIGATIONS BASED ON THEORY AND EXPERIMENT

Authors
HOOCK C KASCH H
Citation
C. Hoock et H. Kasch, REGIOSELECTIVE ACETALIZATION OF ESTRA-4.9 -DIENE-3.17-DIONE - INVESTIGATIONS BASED ON THEORY AND EXPERIMENT, Journal fur praktische Chemie, Chemiker-Zeitung, 337(5), 1995, pp. 358-362
Citations number
21
Categorie Soggetti
Chemistry,"Chemistry Applied
Journal title
Journal fur praktische Chemie, Chemiker-Zeitung → ACNP
ISSN journal
09411216
Volume
337
Issue
5
Year of publication
1995
Pages
358 - 362
Database
ISI
SICI code
0941-1216(1995)337:5<358:RAOE-->2.0.ZU;2-S
Abstract
Semiempirical calculations (AM1) are useful to predict the thermodynam ics of ketalization reactions. The calculated unspecific regioselectiv ity of the ketalization of estra-4.9-dien-3.17-dione (1) with 2.2-dime thylpropanediol using equilibrium conditions was demonstrated experime ntally. Emphasizing kinetic control of the reaction by working at low temperature allowed to synthesize the spiro ketal of 1 in position 3 i n high yield.