PROTONATION OF ALPHA-KETO-ENAMINES

Authors
KUCKLANDER U SCHNEIDER B
Citation
U. Kucklander et B. Schneider, PROTONATION OF ALPHA-KETO-ENAMINES, Archiv der pharmazie, 326(5), 1993, pp. 287-290
Citations number
21
Categorie Soggetti
Chemistry,"Pharmacology & Pharmacy
Journal title
Archiv der pharmazie → ACNP
ISSN journal
03656233
Volume
326
Issue
5
Year of publication
1993
Pages
287 - 290
Database
ISI
SICI code
0365-6233(1993)326:5<287:POA>2.0.ZU;2-2
Abstract
Protonation of cyclohexenone- and cyclopentenone derivatives 2 and 6b, and following enolization in CDC13/CF3COOH is proven. Cyclohexenone d erivative 6a is protonated at the heteroatom. Cycloheptenone 10 is pro tonated at the heteroatom as well as at C-3. On the basis of MNDO- and AM1-calculations the different protonation is explained by sterical h indrance of the coplanarity, and by thermodynamics.