Iodosobenzene
Title: Iodosobenzene
CAS Registry Number: 536-80-1
CAS Name: Iodosylbenzene
Additional Names: PhIO
Molecular Formula: C6H5IO
Molecular Weight: 220.01
Percent Composition: C 32.75%, H 2.29%, I 57.68%, O 7.27%
Literature References: Versatile oxidizing agent. Prepn: C. Willgerodt, Ber. 26, 357 (1893). Synthesis: H. Saltzman, J. G. Sharefkin, Org. Synth. 5, 658 (1973). Mechanistic study: R. M. Moriarty et al., J. Am. Chem. Soc. 103, 686 (1981). Use as oxidant: S. Mukerjee et al., ibid. 119, 8097 (1997); G. Mielniczak, A. Lopusinski, Synlett 2001, 505; as mediator: P. Dauban et al., J. Am. Chem. Soc. 123, 7707 (2001); C.-C. Guo et al., Appl. Catal. A 230, 53 (2002). Brief review: A. Minatti, Synlett 2003, 140-141.
Properties: Yellowish amorphous powder. Explosive if heated to 210° due to disproportion into phenyliodide and iodylbenzene.
Use: Oxygen transfer reagent for stiochiometric or catalytic cross-functionalization of alkenes, alcohols, sulfides, and organometallo compds.

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