Premium
1,3‐cycloaddition of substituted benzonitrile oxides to aliphatic nitriles. The kinetic effect of substituents
Author(s) -
Beltrame Paolo,
Gelli Gioanna,
Loi Aldo
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200636
Subject(s) - benzonitrile , nitrile , chemistry , cycloaddition , ring (chemistry) , medicinal chemistry , oxadiazole , kinetic energy , organic chemistry , catalysis , physics , quantum mechanics
A previous study of the reaction of aromatic nitrile oxides with simple aliphatic nitriles, with the formation of 3,5‐disubstituted 1,2,4‐oxadiazoles, has been extended to a larger number of nitrile oxides. Sixteen new oxadiazole derivatives have been prepared and characterized. Cycloaddition rates have been measured in the temperature range from 50 to 80°. When considering the effect of substituents on the aromatic ring, roughly V‐shaped Hammett plots have been obtained, as already observed for other concerted 1,3‐cycloadditions.