On the Diels-Alder reaction of allenes bearing a diphenylphosphoryl or (trichloromethyl)sulfonyl substituent

Authors
Scheufler, F Maier, ME
Citation
F. Scheufler et Me. Maier, On the Diels-Alder reaction of allenes bearing a diphenylphosphoryl or (trichloromethyl)sulfonyl substituent, EUR J ORG C, (23), 2000, pp. 3945-3948
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
23
Year of publication
2000
Pages
3945 - 3948
Database
ISI
SICI code
1434-193X(200012):23<3945:OTDROA>2.0.ZU;2-0
Abstract
Diels-Alder reactions of two allenes, diphenyl(1,2-propadienyl)phosphane ox ide (4) and 1,2-propadienyltrichloromethyl sulfone (7), with cyclic dienes were studied. While 4 only reacted with cyclopentadiene, to provide the end o adduct 5, the allene 7 proved to be much more reactive. Thus, the cycload dition between 7 and N-Boc-pyrrole gave a mixture of the endo and exo adduc ts 9. The observed reactivities could be rationalized by semiempirical MO c alculations.