CYCLOADDITIONS OF 1-SUBSTITUTED CIS- AND TRANS-2,3-DIPHENYLAZIRIDINES VIA AZOMETHINE YLIDES
1-Benzyl-cis- and -trans-2,3-diphenylaziridines combine at 110 deg C with olefinic dipolarophiles to produce pyrrolidine derivatives in high yields.Stereospecific conrotation for the ring opening of the aziridines to azomethine ylides was deduced from the structure of the cycloadducts.The rate contstants of adduct formation with diethyl fumarate do not depend on the concentration of the dipolarophile.In contrast, ethyl cis- and trans-2,3-diphenylaziridine-1-carboxylate produce with dimethyl fumarate at 145 deg C the same mixture of diastereomeric pyrrolidines both of which are derived from the exo, endo- diphenyl substituted azomethine ylide.
Huisgen, Rolf,Matsumoto, Kiyoshi,Ross, Carl Heinz
p. 1131 - 1136
(2007/10/02)
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