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On the reaction of 1,3-diaza-2-azoniaallene salts with 1,3-butadienes and cumulenes

โœ Scribed by Wolfgang Wirschun; Gerd-Michael Maier; Johannes C. Jochims

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
670 KB
Volume
53
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

1,3-Disubstituted triazenes 3 are oxidized with ten-butyl hypochlorite to N-chlorotriazenes 4, which at low temperatures with antimony pentachloride afford 1,3-diaza-2-azoniaallene salts 5 as reactive intermediates. Cations 5 undergo cycloadditions to one or both double bonds of 1,3-butadienes to furnish 4,5-dihydro-lH-1,2,3-triazolium salts (6a-k) (1,3-dipolar cycloaddition with inverse electron demand). With an allene, a butatriene, and a pentatetraene the 4,5-dihydro-lH-l,2,3-triazolium salts 61-n were obtained. Some of the products undergo consecutive reactions to 1,2,3-triazolium salts (8a,b). The constitutions of 6n and 8b were secured by X-ray structural analyses. 4,5-Dihydro-IH-1,2,3-triazolium salts (6) and lH-l,2,3-triazolium salts (8) are aza analogues of Arduengo's nucleophilic carbenes (imidazolidine-2-ylidenes, imidazole-2-ylidenes).

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