Nitrones—V

descriptionPublicationkeyboard_double_arrow_right Article 01 Jan 1978 English Publisher:Elsevier BVJournal:Tetrahedron, volume 34, pages 1,241-1,245 (issn: 0040-4020,

Authors: Eli Breuer; Shmuel Zbaida;

doi: 10.1016/0040-4020(78)80154-9

Nitrones—V

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Abstract

Abstract Reactions of 3,4-dihydroisoquinoline N-oxide ( 1 ) with carbomethoxymethyldiphenylphosphine oxide ( 13 ) and cyanomethyldiphenylphosphine oxide ( 14 ) lead both in 1,2-dimethoxyethane (DME) and in t-BuOH mostly to enamines 6 and 7 respectively. In contrast reactions of 5,5-dimethyl-Δ 1 -pyrroline N-oxide ( 2 ) with 13 and 14 lead to mixtures of aziridines 8 or 9 and of enamines 10 or 11 , respectively, in the aprotic solvent DME. These reactions give only aziridines 8 or 9 in t-BuOH. The results obtained are explained in terms of the formation of pentacoordinated phosphorus intermediates.

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Hebrew University of Jerusalem
Israel

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