On the Reaction of 1‐Aza‐2‐azoniaallene Salts with Carbodiimides | Zendy

Wang Quanrui | Zendy; Troll Carsten | Zendy; Fischer Helmut | Zendy; Jochims Johannes C. | Zendy; Amer Atef | Zendy

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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 .

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