THERMAL ADDITION-REACTION OF AROYLKETENE WITH 1-ARYL-1-TRIMETHYLSILYLOXYETHYLENES - AROMATIC SUBSTITUENT EFFECTS OF AROYLKETENE AND ARYLTRIMETHYLSILYLOXYETHYLENE ON THEIR REACTIVITY

Authors
SAITOH T OYAMA T SAKURAI K NIIMURA Y HINATA M HORIGUCHI Y TODA J SANO T
Citation
T. Saitoh et al., THERMAL ADDITION-REACTION OF AROYLKETENE WITH 1-ARYL-1-TRIMETHYLSILYLOXYETHYLENES - AROMATIC SUBSTITUENT EFFECTS OF AROYLKETENE AND ARYLTRIMETHYLSILYLOXYETHYLENE ON THEIR REACTIVITY, Chemical and Pharmaceutical Bulletin, 44(5), 1996, pp. 956-966
Citations number
21
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
44
Issue
5
Year of publication
1996
Pages
956 - 966
Database
ISI
SICI code
0009-2363(1996)44:5<956:TAOAW1>2.0.ZU;2-D
Abstract
The thermal addition reaction of various aroylketenes (C) generated by the thermolysis of 5-aryldioxofurans (A) to 1-aryl-1-trimethylsilylox yethylenes gave 1,5-diarylpentane-1,3,5-triones (D) and 2,6-diaryl-4H- pyran-4-ones (E). The introduction of electron withdrawing substituent s in the aroylketene and of electron donating substituents facilitated the addition reaction. The observed substituent effects and the react ion mechanism are interpreted in terms of molecular orbital analyses.