Structure and Chemistry of Hypervalent Iodine Heterocycles: Acid-Catalyzed Rearrangement of Benziodazol-3-ones to 3-Iminiumbenziodoxoles

VV Zhdankin, RM Arbit, BJ Lynch, P Kiprof…

Index: Zhdankin, Viktor V.; Arbit, Ruslan M.; Lynch, Benjamin J.; Kiprof, Paul; Young Jr., Victor G. Journal of Organic Chemistry, 1998 , vol. 63, # 19 p. 6590 - 6596

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Citation Number: 36

Abstract

New 1-substituted benziodazoles, namely, azide 7, tosylate 8, mesylate 9, and triflate 10, were prepared by the reaction of acetoxybenziodazole 3 with TMSN3, TsOH⊙ H2O, MsOH, or TMSOTf, respectively. Reaction of triflate 10 with alcohols (methanol, ethanol, 2-propanol, and 2-adamantanol) afforded novel 1-alkoxy-3-iminiumbenziodoxoles 11a-d, while similar reactions with amides gave 1-amido-3-iminiumbenziodoxoles 12a-d in 51-89% yield. The ...