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Synthesis of Nonenolizing 2‐Acylcyclohex‐2‐enones
Author(s) -
OliveiraFerrer Leticia,
Schmidt Kerstin,
Margaretha Paul
Publication year - 2001
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20011219)84:12<3818::aid-hlca3818>3.0.co;2-r
Subject(s) - chemistry , vicinal , enone , steric effects , double bond , ring (chemistry) , group (periodic table) , carbonyl group , stereochemistry , atom (system on chip) , organic chemistry , computer science , embedded system
Cyclohexanones 2b and 2c represent the first examples of nonenolizing 2‐acylcyclohex‐2‐enones, as they bear H‐atoms neither at C(4) or C(6) of the enone ring, nor at the C‐atom vicinal to the exocyclic carbonyl group. While the CF 3 CO group in 2b (and the Ac group in 2a ) are coplanar to the enone double bonds, the pivaloyl group in 2c , for steric reasons, is out of plane. Compounds 2 exhibit a pronounced sluggishness in both thermal and light‐induced bimolecular reactions.