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

✍ Scribed by György Keglevich; Mónika Trecska; Beáta Dajka; Béla Pete; András Dobó; László Tőke

Publisher: John Wiley and Sons
Year: 2000
Tongue: English
Weight: 102 KB
Volume: 11
Category: Article
ISSN: 1042-7163
DOI: 10.1002/1098-1071(2000)11:4<271::aid-hc5>3.0.co;2-t

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✦ Synopsis

2,4,6-Trialkylphenylphospholes 3a

(R‫ס‬Me), 3b (R‫ס‬i-Pr) and 3c (R‫ס‬t-Bu), with increasing flattening at phosphorus and hence with increasing electron delocalisation, 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 2 J PC NMR couplings and by an independent synthesis.

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