二乙酸亚碘酰苯

• 产品号: B24531
• CAS号: 3240-34-4
• 分子式: C10H11IO4
• 分子量: 322.09641
• 纯 度: 98+%

产品别名

• 标题: Iodosobenzene diacetate
• IUPAC标准名: (acetyloxy)(phenyl)-λ^3-iodanyl acetate
• IUPAC传统名: phenyliodosodiacetate
• 别名: DIB; (Diacetoxyiodo)benzene

产品登记号

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

产品性质

• 纯度: 98+%
• 熔点: 159-161°C
• GHS危险声明: H315-H319-H335
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• GHS警示性声明: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 危险公开号: 36/37/38
• RTECS编号: DA3525000
• 安全公开号: 26-37
• 保存注意事项: Light Sensitive
• TSCA收录: 是

参考文献

• 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).