The Journal of Organic Chemistry

Hydrogen cyanide chemistry. 9. Cycloaddition reactions and nitrenium ion type reactivity of diiminosuccinonitrile

T Fukunaga, RW Begland

Index: Fukunaga, Tadamichi; Begland, Robert W. Journal of Organic Chemistry, 1984 , vol. 49, p. 813 - 821

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Citation Number: 9

Abstract

Cycloaddition reactions of diiminosuccinonitrile (DISN) with nucleophilic olefins yield a variety of products including [4+ 21 cycloadducts and aziridines. All of the products derived from l, &dienes, styrene, para-substituted styrenes, cycloheptatriene, norbornene, and norbornadiene can be accounted for by rearrangements of a common intermediate, zwitterionic aziridinium ion. We introduce the concept of reverse polarization and propose ...