CONJUGATE ADDITION OF WATER TO ALPHA-CARBONYLCARBENES

Authors
CHIANG Y JEFFERSON EA KRESGE AJ POPIK VV XIE RQ
Citation
Y. Chiang et al., CONJUGATE ADDITION OF WATER TO ALPHA-CARBONYLCARBENES, Journal of physical organic chemistry, 11(8-9), 1998, pp. 610-613
Citations number
20
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Journal of physical organic chemistry → ACNP
ISSN journal
08943230
Volume
11
Issue
8-9
Year of publication
1998
Pages
610 - 613
Database
ISI
SICI code
0894-3230(1998)11:8-9<610:CAOWTA>2.0.ZU;2-O
Abstract
alpha-Carbonylcarbenes (2a-c) generated by UV photolysis of 2-diazophe nylacetic acid (1a), its methyl ester (1b) and 4-diazo-3-isochromanone (1c) in aqueous solution undergo conjugate addition of water across t he entire carbonylcarbene moiety to give enols (3a-c) of the correspon ding alpha-hydroxycarbonyl compounds. These carbenes are long-lived, w ith microsecond lifetimes in aqueous solution. (C) 1998 John Wiley & S ons, Ltd.