Interconversion of Nitrenes, Azirenes, and Diradicals: Rearrangement of 3-Isoquinolylnitrene to o-Cyanophenylketenimine and 1-Cyanoisoindole

M Vosswinkel, H Lüerssen, D Kvaskoff…

Index: Vosswinkel, Michael; Lueerssen, Holger; Kvaskoff, David; Wentrup, Curt Journal of Organic Chemistry, 2009 , vol. 74, # 3 p. 1171 - 1178

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Citation Number: 14

Abstract

Photolysis of tetrazolo [1, 5-b] isoquinoline/3-azidoisoquinoline 22T/22A generates 3- isoquinolylnitrene 23, which has been characterized together with a diradical species (25) by Ar matrix ESR spectroscopy. Photolysis at λ> 300 nm generates azirene 24, characterized by IR spectroscopy, whereas further broad-band UV photolysis destroys the azirene to produce o-cyanophenylketenimine 17. The use of 15N-labeled tetrazole/azide ...