Journal
TETRAHEDRON LETTERS
Volume 46, Issue 36, Pages 6023-6027Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.07.012
Keywords
hypervalent iodine; electrospray ionization mass spectrometry; lodobenzene diacetate; lodobenzene bis(trifluoroacetate)
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Solutions of iodobenzene diacetate in CH3CN, AcOH, MeOH/H2O and MeOH (with or without base) were analyzed by electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (ESI-MS/MS). The major species in CH3CN, AcOH and MeOH/H2O solutions are [PhI(OAc)(2)Na](+), [Pbl(OAC)(2)K]+, [PhI](+), [PhIOAc](+), [PhIOH](+), [PhIO2Ac](+), [PhIO2H](+) and the dimer [Ph2I2O2Ac](+). On the other hand, MeOH solutions showed [PhIOMe](+) as the most abundant species. A similar result was observed adding 2, 3 or 4 equiv of KOH to MeOH solutions. However, in the presence of 10 equiv of KOH, probably occurs the formation of a polymeric material. Similarly, ESI-MS analysis of the MeOH solution of iodobenzene bis(trifluoroacetate) showed a pattern analogous to that observed for the corresponding solutions of PhI(OAc)(2). However, ESI-MS spectral data of PhI(O2CCF3)(2) of CH3CN suggests that the main species in solutions is iodosylbenzene, which contrasts with the results obtained for PhI(OAC)(2). (c) 2005 Elsevier Ltd. All rights reserved.
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