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On the Diels−Alder Reaction of Allenes Bearing a Diphenylphosphoryl or (Trichloromethyl)sulfonyl Substituent
Author(s) -
Scheufler Frank,
Maier Martin E.
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200012)2000:23<3945::aid-ejoc3945>3.0.co;2-6
Subject(s) - chemistry , cyclopentadiene , allene , cycloaddition , adduct , substituent , diels–alder reaction , sulfonyl , sulfone , medicinal chemistry , nitrone , organic chemistry , catalysis , alkyl
Diels−Alder reactions of two allenes, diphenyl(1,2‐propadienyl)phosphane oxide ( 4 ) and 1,2‐propadienyltrichloromethyl sulfone ( 7 ), with cyclic dienes were studied. While 4 only reacted with cyclopentadiene, to provide the endo adduct 5 , the allene 7 proved to be much more reactive. Thus, the cycloaddition between 7 and N ‐Boc‐pyrrole gave a mixture of the endo and exo adducts 9 . The observed reactivities could be rationalized by semiempirical MO calculations.