(Bis(trifluoroacetoxy)iodo)benzene

(Bis(trifluoroacetoxy)iodo)benzene changed changed 477200856 (bis(trifluoroacetoxy)iodo)benzene.png 150px skin-invert (bis(trifluoroacetoxy)iodo)benzene-3D-balls.png 150px 1,1′-[(Phenyl-λ3-iodanediyl)bis(oxy)]bis(2,2,2-trifluoroethan-1-one) Phenyliodine bis(trifluoroacetate); PIFA 1/C10H5F6IO4/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16/h1-5H PEZNEXFPRSOYPL-UHFFFAOYAA correct chemspider 1S/C10H5F6IO4/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16/h1-5H correct chemspider PEZNEXFPRSOYPL-UHFFFAOYSA-N changed ?? 2712-78-9 102317 correct chemspider 92428 220-308-0 659SFV27XS FC(F)(F)C(=O)OI(OC(=O)C(F)(F)F)c1ccccc1 10 5 6 1 4 07 Warning 315 319 335 261 264 271 280 302+352 304+340 305+351+338 312 321 332+313 337+313 362 403+233 405 501 (Bis(trifluoroacetoxy)iodo)benzene, C 6 H 5 I(OCOCF 3 ) 2, is a hypervalent iodine compound used as a reagent in organic chemistry. It can be used to carry out the Hofmann rearrangement under acidic conditions. Preparation The syntheses of all aryl hypervalent iodine compounds start from iodobenzene. The compound can be prepared by reaction of iodobenzene with a mixture of trifluoroperacetic acid and trifluoroacetic acid in a method analogous to the synthesis of (diacetoxyiodo)benzene: frameless|400px|center It can also be prepared by dissolving diacetoxyiodobenzene (a commercially available compound) with heating in trifluoroacetic acid: frameless|500px|center Uses It also brings around the conversion of a hydrazone to a diazo compound, for example in the diazo-thioketone coupling. It also converts thioacetals to their parent carbonyl compounds. Hofmann rearrangement The Hofmann rearrangement is a decarbonylation reaction whereby an amide is converted to an amine by way of an isocyanate intermediate. It is usually carried out under strongly basic conditions. Everett S. Wallis Lane John F. The Hofmann Reaction Organic Reactions 1946 3 7 267–306 10.1002/0471264180.or003.07 Hofmann Reaction 134–136 Name Reactions in Organic Chemistry Alexander R. Surrey 2nd Academic Press 1961 9781483258683 https://books.google.com/books?id=JSESBQAAQBAJ&pg=PA134 500px The reaction can also be carried out under mildly acidic conditions by way of the same intermediate using a hypervalent iodine compound in aqueous solution. 6.15 Hofmann, Curtius, Schmidt, Lossen, and Related Reactions Jeffrey Aubé Charlie Fehl Ruzhang Liu Michael C. McLeod Hashim F. Motiwala Heteroatom Manipulations Comprehensive Organic Synthesis II 1993 6 598–635 10.1016/B978-0-08-097742-3.00623-6 9780080977430 An example published in Organic Syntheses is the conversion of cyclobutanecarboxamide, easily synthesized from cyclobutylcarboxylic acid, to cyclobutylamine. The primary amine is initially present as its trifluoroacetate salt, which can be converted to the hydrochloride salt to facilitate product purification. Almond M. R. Stimmel J. B. Thompson E. A. Loudon G. M. 132 66 1988 cv8p0132 Hofmann Rearrangement Under Mildly Acidic Conditions Using [I,I-Bis(Trifluoroacetoxy)]Iodobenzene: Cyclobutylamine Hydrochloride from Cyclobutanecarboxamide 10.15227/orgsyn.066.0132 8 132 400px References Category:Iodanes Category:Reagents for organic chemistry Category:Phenyl compounds Category:Trifluoroacetates Category:Iodine(III) compounds