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Regiochemistry of the cycloaddition of nitrilium N-phenylimides to dibenzalacetone: A reinvestigation

✍ Scribed by Hassan A. Albar; Magda A. Abdallah; Mosselhi A. N. Mosselhi; Ahmad S. Shawali

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 376 KB
Volume: 7
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(199608)7:4<225::aid-hc2>3.0.co;2-4

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✦ Synopsis

Reaction of benzonitrilium N-phenylimide 3a with dibenzalacetone 1 yielded a mixture of the mono-and biscycloadducts 8a and 1 la in a I:I ratio. A similar reaction of' 1 with ethoxycarbonylnitrilium N-phenylimide 3b afforded a mixture of the cycloadducts 7b, 8b, and 12b in a 1:3:6 ratio, respectively. The structures of these products were established by spectral analyses and chemical transformations. The results invalidate the previously reported structure 4a assigned for the biscycloadduct isolated from the reaction of 3a with 1.

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