Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 12, Pages 2387-2394Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200901520
Keywords
Nucleophilic addition; Amination; Nucleophilic substitution; Nitrogen heterocycles; Transition states
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2-Aryl(arylsulfony1)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ones and 3-arylimino-6,7-dihydroimidazo[2,1-c][1,2,4]thiadiazoles have been synthesized by intramolecular nucleophilic substitution reactions at the electron-deficient sp(2) nitrogen atom of 2-(hydroxyimino)imidazolidine O-sulfonate. The displacement of the sulfate leaving group by both nitrogen and sulfur anionic nucleophiles proceeds exothermically by in-plane S(N)2 sigma nucleophilic substitution.
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