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On the Reaction of 1‐Aza‐2‐azoniaallene Salts with Carbodiimides
Author(s) -
Wang Quanrui,
Troll Carsten,
Fischer Helmut,
Jochims Johannes C.,
Amer Atef
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931261128
Subject(s) - chemistry , geminal , cycloaddition , medicinal chemistry , stereochemistry , organic chemistry , catalysis
1‐Aza‐2‐azoniaallene cations 3 , prepared in situ from geminal (chloroalkyl)azo compounds 2 , react with carbodiimides 4 to give 4,5‐dihydro‐5‐imino‐1 H ‐1,2,4‐triazolium salts 7 . An X‐ray structural analysis was carried out for 71 . According to AM1 calculations the cycloaddition of carbodiimides to 1‐aza‐2‐azoniaallene cations occurs in a nonconcerted manner via cyanamidium cations 5 as intermediates. Hetero‐Wagner‐Meerwein rearrangements of the primary cycloadducts 6 provide the final products 7 .