57499-70-4

Upstream product

• 13257-51-7 mercury(II) trifluoroacetate 
• 110-83-8 cyclohexene 
• 407-25-0 trifluoroacetic anhydride 
• 626-62-0 Cyclohexyl iodide 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 108164-34-7 C₇H₇F₆IO₄ 
• 131846-61-2 1-(2-iodo-1-trifluoroacetoxy-ethyl)-benzene 
• 2923-19-5 thallium(I) trifluoroacetate 
• 14353-86-7 iodine tris(trifluoroacetate) 
• 34701-03-6 trans-1-bromo-2-iodocyclohexane 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 43123-07-5 cis-2-hydroxycyclohexyl 2,2,2-trifluoroacetate 
• 1792-81-0 cis-1,2-cyclohexane 
• 41049-51-8 cis-1,2-cyclohexylene bis(trifluoroacetate) 
• 27088-69-3 trans-1,2-cyclohexylene bis(trifluoroacetate) 

Relevant academic research and scientific papers

OXIDATION OF ALKENES BY THE Pb(IV)-I2-CF3COOH SYSTEM

The Pb(OAc)4-I2-CF3COOH oxidizing system was discovered, and its reactions with alkenes (cyclohexene, 1-hexene, styrene) in 1,2,2-trifluorotrichloroethane led to the selective formation of β-iodoalkyl trifluoroacetates or the ditrifluoroacetates of diols.In the reaction with 1-hexene a third direction is possible, i.e., the formation of the mixed acetic acid and trifluoroacetic diesters of 1,2-hexanediol.During the oxidation of styrene the formation of the geminal diester 1,1-ditrifluoroacetoxy-2-phenylethane is observed.The reaction takes place with the intermediate formation of compounds of monovalent iodine or a complex of polyvalent iodine, depending on the ratio of the reagents.

BROMO- AND IODOFUNCTIONALIZATION OF OLEFINS BY MEANS OF THE MERCURY(II) SALT-HALOGEN COMBINATION

Mercury(II) salts (fluoride, chloride, bromide, formate, acetate, trifluoroacetate, propionate, benzoate, nitrate, methanesulphonate, toluene-p-sulphonate, thiocyanate, and toluene-p-sulphinate) reacted with monoolefines and bromine or iodine to give 1,2-bifunctionalized products resulting from the addition of the halogen and the mercury(II) salt anion selectively.The addition was regiospecific for styrene and for 3,3-dimethylbut-1-ene affording Markownikoff type products, respectively.In the case of hex-1-ene both regioisomers were obtained.For cyclic alkenes trans-1,2-derivatives were stereoselectively obtained.Cycloocta-1,5-diene gave the monoaddition products.Buta-1,3-diene underwent mainly 1,2-addition and allylic derivatives gave the corresponding 1,2,3-trifunctionalized compounds.A possible ionic mechanism is proposed to explain the obtained addition products.

NOVEL REAGENTS CONTAINING HYPERVALENT IODINE AND THEIR USE FOR ELECTROPHILIC ADDITIONS TO OLEFINS

A series of novel I(III) containing reagents have been developed and their electrophilic reactions with olefins giving vic-disubstituted derivatives (including vic-ditriflates) are described.

Oxidative Displacement of Halogen from Alkyl Halides by Phenyliodine(III) Dicarboxylates

The reaction of alkyl iodides with aryliodine(III) dicarboxylates affords as the main product the ester derived through substitution of iodine by an acyloxy group; in some cases α-iodoalkyl esters are also formed along with other minor products.Certain reactive bromides and chlorides react along similar lines.The mechanism of these reactions is briefly discussed.