I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.
Iodosobenzene is used as an oxidizing and acetoxylating agent in organic synthesis. It is actively involved in the preparation of (Z)-3,7-dimethyl-2,6-octadien-1-al(neral) from (Z)-3,7-dimethyl-2,6-octadien-1-ol (nerol) in presence of 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO). It is a useful reagent for the synthesis of a wide variety of heterocyclic compounds. It is also used in the Pd-catalyzed 2-arylation of indoles.
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 ß-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).
Wu, J.; Hoang, K. L. M.; Leow, M. L.; Liu, X. W. Pd-catalyzed cross-coupling of aromatic compounds with carboxylic acids via C-H bond activation. Org. Chem. Front. 2015, 2 (5), 502-505.
Ghosh, S.; Chaudhuri, S.; Bisai, A. Oxidative Dimerization of 2-Oxindoles Promoted by KO t Bu-I2: Total Synthesis of (±)-Folicanthine. Org. Lett. 2015, 17 (6), 1373-1376.
Hazard Statements: H302-H312-H315-H319-H335
Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant