Syntheses and 15N NMR Spectra of Iminodiaziridines–Ring??Expansions of 1??Aryl??3??iminodiaziridines to 1H??and 3aH??Benzimidazoles, 2H??Indazoles, and 5H?? …

…, KH Ross, G Philipp, M Hagedorn…

Index: Quast, Helmut; Ross, Karl-Heinz; Philipp, Gottfried; Hagedorn, Manfred; Hahn, Harald; Banert, Klaus European Journal of Organic Chemistry, 2009 , # 23 p. 3940 - 3952

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Citation Number: 5

Abstract

Abstract Iminodiaziridines are synthesized by (i) 1, 3-dehydrochlorination with potassium tert- butoxide of N-chloroguanidines, generated in situ from N, N′, N ″-substituted guanidines with tert-butyl hypochlorite, and (ii) base-mediated 1, 3-elimination of sulfuric acid from N, N′, N ″-substituted hydroxyguanidine O-sulfonic acids. At elevated temperatures,( alkylimino) diaziridines undergo valence isomerization by 1, 3-shift,[2+ 1] cycloelimination ...