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Conjugate addition of water to α-carbonylcarbenes

✍ Scribed by Y. Chiang; E. A. Jefferson; A. J. Kresge; V. V. Popik; R.-Q. Xie

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 115 KB
Volume: 11
Category: Article
ISSN: 0894-3230
DOI: 10.1002/(sici)1099-1395(199808/09)11:8/9<610::aid-poc43>3.0.co;2-l

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✦ Synopsis

a-Carbonylcarbenes (2a-c) generated by UV photolysis of 2-diazophenylacetic acid (1a), its methyl ester (1b) and 4-diazo-3-isochromanone (1c) in aqueous solution undergo conjugate addition of water across the entire carbonylcarbene moiety to give enols (3a-c) of the corresponding a-hydroxycarbonyl compounds. These carbenes are long-lived, with microsecond lifetimes in aqueous solution.

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