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Conjugate addition of water to α‐carbonylcarbenes
Author(s) -
Chiang Y.,
Jefferson E. A.,
Kresge A. J.,
Popik V. V.,
Xie R.Q.
Publication year - 1998
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199808/09)11:8/9<610::aid-poc43>3.0.co;2-l
Subject(s) - chemistry , conjugate , aqueous solution , moiety , diazo , photodissociation , microsecond , photochemistry , medicinal chemistry , organic chemistry , mathematical analysis , physics , mathematics , astronomy
α‐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 α‐hydroxycarbonyl compounds. These carbenes are long‐lived, with microsecond lifetimes in aqueous solution. © 1998 John Wiley & Sons, Ltd.