Intramolecular 1,3-dipolar cycloaddition is an extremely versatile and important reaction. The range of synthetic possibilities which it opens for the construction of fused heterocycles is extremely large. 1 With azides, intra-
Analysis of an intermediate in a 1,3-dipolar cycloaddition of methylsulfonyl azide
β 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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β¦ Synopsis
Abstract
MNDOβPM3 calculations, carried out on an experimentally determined structure of an intermediate in the cycloaddition of an electrophilic azide and a nucleophilic 1,3βdipolarophile, 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.
π SIMILAR VOLUMES
## Abstract Cyclic ketene __N,N__βacetals derived from imidazolidine (4a, c) and 2,3βdihydrobenzimidazole (6aβc) add methanesulphonyl azide (2a) or picryl azide (2f) to afford the zwitterions 5 and 7, respectively. The structure of 7d is elucidated by Xβray crystallography. Reversibility of formati
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