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Journal of the Chemical Society C Organic

Article . 1966 . Peer-reviewed

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Nitrones. Part III. Photolysis of cyclic nitrones

Name: Nitrones. Part III. Photolysis of cyclic nitrones
Keywords: 3. Good health

descriptionPublicationkeyboard_double_arrow_right Article 01 Jan 1966 English Publisher:Royal Society of Chemistry (RSC)Journal:Journal of the Chemical Society C: Organic (issn: 0022-4952,

Authors: L. S. Kaminsky; M. Lamchen;

doi: 10.1039/j39660002295

Nitrones. Part III. Photolysis of cyclic nitrones

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Abstract

Ultraviolet irradiation of 2-substituted 1-pyrroline 1-oxides yielded corresponding bicyclic oxaziridines. Prolonged irradiation of the 3,3,5-trimethyl-6-oxa-1-azabicyclo[3,1,0]hexane gave an N-acetylazetidine and a pyrroline. Acid hydrolyses of 2,2,5- and 3,3,5-trimethyl-6-oxa-1-azabicyclo[3,1,0]hexane yielded acetonylacetone and 3,3-dimethylpentan-5-al-2-one, respectively. The synthesis of the nitrone 3,3,5-trimethyl-1-pyrroline 1-oxide and its irradiation to form an oxaziridine is described. Prolonged irradiation of the latter yielded a pyrrolidinone.

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