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Analysis of an intermediate in a 1,3-dipolar cycloaddition of methylsulfonyl azide

✍ Scribed by Reiner Sustmann; Willi Sicking; Helmut Quast


Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
344 KB
Volume
13
Category
Article
ISSN
0192-8651

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✦ Synopsis


Abstract

MNDO‐PM3 calculations, carried out on an experimentally determined structure of an intermediate in the cycloaddition of an electrophilic azide and a nucleophilic 1,3‐dipolarophile, show that the semiempirical MO scheme models this structure closely. Transition structures for formation of the intermediate and ring closure of the latter are described.


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## Abstract Cyclic ketene __N,N__‐acetals derived from imidazolidine (4a, c) and 2,3‐dihydrobenzimidazole (6a–c) add methanesulphonyl azide (2a) or picryl azide (2f) to afford the zwitterions 5 and 7, respectively. The structure of 7d is elucidated by X‐ray crystallography. Reversibility of formati