THE CHEMISTRY OF 5-OXODIHYDROISOXAZOLES .5. THE PHOTOLYSIS OF 2-PHENYLISOXAZOL-5(2H)-ONE IN ALCOHOLS

Ethyl 5-oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxylate(1) has been photolysed in methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, t-butyl alcohol, allyl alcohol and propargyl alcohol, and the products characterised. Two types of photo products are formed: methanetricarboxylic acid derivatives...

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Bibliographic Details
Published inTetrahedron Vol. 48; no. 41; pp. 9073 - 9084
Main Authors ANG, KH, PRAGER, RH
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 09.10.1992
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
KETENES
SULFIDES
ISOXAZOLONES
ALIPHATIC CLAISEN REARRANGEMENT
PHOTOLYSIS
IMINOCARBENES
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Summary:Ethyl 5-oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxylate(1) has been photolysed in methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, t-butyl alcohol, allyl alcohol and propargyl alcohol, and the products characterised. Two types of photo products are formed: methanetricarboxylic acid derivatives resulting from alcohol capture of the first formed ketene, and 2-alkoxy-3-phenylaminoacrylates, formed by capture, by the alcohol, of the imino-carbene arising from (1) by loss of carbon dioxide.
ISSN:0040-4020
DOI:10.1016/S0040-4020(01)82002-0