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

G. Keglevich, Mónika Trecska, Beáta Dajka, Béla Pete, A. Dobó, L. Tőke

Research output: Contribution to journalArticle

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 - 2000

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Cycloaddition
Phosphorus
Nuclear magnetic resonance
Oxidation
Electrons
N-phenylmaleimide

ASJC Scopus subject areas

  • Chemistry(all)

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Diels-Alder reaction of (2,4,6-trialkylphenyl)phospholes with N-phenylmaleimide. / Keglevich, G.; Trecska, Mónika; Dajka, Beáta; Pete, Béla; Dobó, A.; Tőke, L.

In: Heteroatom Chemistry, Vol. 11, No. 4, 2000, p. 271-275.

Research output: Contribution to journalArticle

Keglevich, G. ; Trecska, Mónika ; Dajka, Beáta ; Pete, Béla ; Dobó, A. ; Tőke, L. / Diels-Alder reaction of (2,4,6-trialkylphenyl)phospholes with N-phenylmaleimide. In: Heteroatom Chemistry. 2000 ; Vol. 11, No. 4. pp. 271-275.
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AU - Dobó, A.

AU - Tőke, L.

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