Iodosobenzene diacetate

• Catalog No.: B24531
• CAS Number: 3240-34-4
• M. F.: C10H11IO4
• M. W.: 322.09641
• Purity: 98+%

SYNONYMS

• Title: 二乙酸亚碘酰苯
• IUPAC name: (acetyloxy)(phenyl)-λ^3-iodanyl acetate
• IUPAC Traditional name: phenyliodosodiacetate
• Synonyms: DIB; (Diacetoxyiodo)benzene

DATABASE IDS

• CAS Number: 3240-34-4
• EC Number: 221-808-1
• MDL Number: MFCD00008692
• Beilstein Number: 1879369

PROPERTIES

• Purity: 98+%
• Melting Point: 159-161°C
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• RTECS: DA3525000
• Safety Statements: 26-37
• Storage Warning: Light Sensitive
• TSCA Listed: 是

REFERENCES

• Versatile oxidizing and acetoxylating agent.
• For a review of the ɑ-functionalization of carbonyl compounds by hypervalent iodine reagents, see: Contemp. Org. Synth., 2, 121 (1995).
• Hydrazine hydrate is oxidized to the useful cis-reducing agent diimide: Synth. Commun., 17, 703 (1987).
• Converts primary aliphatic amides to amines, by Hofmann degradation: J. Org. Chem., 44, 1746 (1979); Synthesis, 266 (1981); 31 (1983). For use in the synthesis of ?-alanine derivatives, see: J. Org. Chem., 62, 6918 (1997); for reaction scheme, see N(ɑ)-Benzyloxycarbonyl-L-asparagine, L08592.
• In the presence of triethyl orthoformate, aryl ethyl ketones undergo a rearrangement to ɑ-methyl arylacetates: Synthesis, 231 (1984):
  
• Similarly, in the presence of an orthoformate and sulfuric acid, flavanones undergo a 1,2-aryl shift to give 2-aryl-2,3-dihydrobenzofuran-3-carboxylates: Bull. Chem. Soc. Jpn., 68, 1168 (1995). However, iodosobenzene diacetate alone oxidizes flavanones to flavones: J. Chem. Res. (Synop.), 213 (1995). For a review of the use of the reagent in heterocyclic synthesis, see: Synlett, 221 (1994).
• Useful reagent for mild, rapid cleavage of 1,3-dithianes to the parent carbonyl compounds: Syn. Commun., 30, 4081 (2000).
• In combination with iodine, forms the acyl hypoiodite, which adds to alkenes: Bull. Chem. Soc. Jpn., 41, 1476 (1968), iodinates alkylbenzenes: J. Am. Chem. Soc., 90, 6187 (1968), and effects the decarboxylative iodination of aromatic carboxylic acids: Synth. Commun., 18, 1327 (1988).
• See cis,cis-1,5-Cyclooctadiene, B21196, for an intramolecular cyclization reaction.
• For use in the Pd(II)-catalyzed functionalization of sp² and sp³ C-H bonds, see: J. Am. Chem. Soc., 126, 2300 (2004).
• Treatment with aqueous NaOH gives the useful selective oxidant iodosobenzene (iodosylbenzene): Org. Synth. Coll., 5, 658 (1973).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 657 (2006). For reviews of the use of polyvalent iodine compounds in organic synthesis, see: Synthesis, 709 (1984); Acc. Chem. Res., 19, 244 (1986); Chem. Rev., 96, 1123 (1996). For a monograph, see: A Varvoglis, The Organic Chemistry of Polycoordinated Iodine, VCH, N.Y. (1992).