Diels-Alder reaction of (2,4,6-trialkylphenyl)phospholes with N-phenylmaleimide

György Keglevich, Mónika Trecska, Beáta Dajka, Béla Pete, András Dobó, László Toke

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13 Citations (Scopus)

Abstract

2,4,6-Trialkylphenylphospholes 3a (R = Me), 3b (R = i-Pr) and 3c (R = t-Bu), with increasing flattening at phosphorus and hence with increasing electron delocalization, underwent the Diels-Alder reaction with N-phenylmaleimide to give predominantly cycloadducts 4a-c with the trialkylphenyl substituents anti to the phosphanorbornene double bond. With increasing aromaticity, the cycloaddition was slower. The stereostructure of the products (6 and 7) obtained after oxidation was confirmed by stereospecific 2JpC NMR couplings and by an independent synthesis.

Original languageEnglish
Pages (from-to)271-275
Number of pages5
JournalHeteroatom Chemistry
Volume11
Issue number4
DOIs
Publication statusPublished - Jan 1 2000

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ASJC Scopus subject areas

  • Chemistry(all)

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