Journal
MINI-REVIEWS IN ORGANIC CHEMISTRY
Volume 1, Issue 3, Pages 291-308Publisher
BENTHAM SCIENCE PUBL LTD
DOI: 10.2174/1570193043403181
Keywords
alpha-diazo carbonyl compounds; C-13-labelling; oxirenes; alpha-oxocarbenes; photochemistry; rearrangement mechanisms
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Evidence obtained by carbon labelling and carbene-scavenging techniques for the establishment of an alpha-oxocarbene-oxirene interconversion in the photolysis of acyclic alpha-diazoketones is summarised. Normal-sized alicyclic alpha-diazoketones and o-quinone diazides react without intervention of the oxirene route, whereas the 12-membered ring system behaves like the acyclic counterparts. The oxirene participation is discussed with reference to stereochemical features of the alpha-diazoketones and predictions derived from high-level theory.
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