Unexpected [2+2] cycloaddition between the P=O group of P-(2,4,6-triisopropylphenyl) P-heterocycles and dimethyl acetylenedicarboxylate

Authors
Keglevich, G Forintos, H Szollosy, A Toke, L
Citation
G. Keglevich et al., Unexpected [2+2] cycloaddition between the P=O group of P-(2,4,6-triisopropylphenyl) P-heterocycles and dimethyl acetylenedicarboxylate, CHEM COMMUN, (15), 1999, pp. 1423-1424
Citations number
9
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
15
Year of publication
1999
Pages
1423 - 1424
Database
ISI
SICI code
1359-7345(1999):15<1423:U[CBTP>2.0.ZU;2-1
Abstract
The reaction of 1-(2,4,6-triisopropylphenyl)-1,2-dihydrophosphinine 1-oxide 1d with dimethyl acetylenedicarboxylate (DMAD) affords, surprisingly, oxap hosphetene 3 instead of the expected Diels-Alder cycloadduct; the unusual r eactivity of the trialkylphenylphosphine oxides towards DMAD seems to be of general value.