Oxirene Participation in the Photochemical Wolff Rearrangementa

Title: Oxirene Participation in the Photochemical Wolff Rearrangementa

Volume: 1 Issue: 3

Author(s): K.- P. Zeller, A. Blocher and P. Haiss

Affiliation:

Keywords: diazo carbonyl compounds, 13c-labelling, oxirenes, oxocarbenes, photochemistry, rearrangement mechanisms

Abstract: Evidence obtained by carbon labelling and carbene-scavenging techniques for the establishment of an α-oxocarbene-oxirene interconversion in the photolysis of acyclic α-diazoketones is summarised. Normalsized alicyclic α-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 α-diazoketones and predictions derived from high-level theory.

Cite this article as:

Zeller P. K.-, Blocher A. and Haiss P., Oxirene Participation in the Photochemical Wolff Rearrangementa, Mini-Reviews in Organic Chemistry 2004; 1 (3) . https://dx.doi.org/10.2174/1570193043403181