+ Site Statistics
References:
52,654,530
Abstracts:
29,560,856
PMIDs:
28,072,755
+ Search Articles
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ PDF Full Text
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Translate
+ Recently Requested

New and efficient syntheses of alpha-iodo-alpha,alpha-difluoro- and beta-iodo-alpha,alpha,beta,beta-tetrafluorocarboxylic acid derivatives as useful building blocks for making functional fluoro compounds



New and efficient syntheses of alpha-iodo-alpha,alpha-difluoro- and beta-iodo-alpha,alpha,beta,beta-tetrafluorocarboxylic acid derivatives as useful building blocks for making functional fluoro compounds



Journal of Organic Chemistry 69(1): 198-201



Perfluoroolefins reacted with I-Cl and ClSO(3)H under mild conditions to give R(F)CFICF(2)OSO(2)Cl, which could be readily converted into various alpha-iodo-perfluorocarboxylic acid derivatives or telomerized with tetrafluoroethylene to I(CF(2)CF(2))(n)()OSO(2)Cl. Ring-opening reaction of perfluoroalkoxypentafluorocyclopropane with iodine at 240 degrees C produced ICF(2)CF(2)COF, which was quenched by alcohol, water, or NH(3) to give beta-iodo-alpha,alpha,beta,beta-tetrafluorocarboxylic acid derivatives. These functional fluorinated iodides can be used as building blocks for making selectively fluorinated compounds.

(PDF emailed within 0-6 h: $19.90)

Accession: 012351190

Download citation: RISBibTeXText

PMID: 14703399

DOI: 10.1021/jo035170j


Related references

Pharmacological characterization of recombinant human neuronal nicotinic acetylcholine receptors h alpha 2 beta 2, h alpha 2 beta 4, h alpha 3 beta 2, h alpha 3 beta 4, h alpha 4 beta 2, h alpha 4 beta 4 and h alpha 7 expressed in Xenopus oocytes. Journal of Pharmacology and Experimental Therapeutics 280(1): 346-356, 1997

Conjugate addition reactions of alpha-aminoalkylcuprates with alpha, beta-alkenyl-, alpha,beta-alkynyl-, alpha,beta-beta,gamma-allenyl-, and alpha,beta-gamma,delta-dienyl carboxylic acid derivatives, nitriles, and sulfoxides. Journal of Organic Chemistry 65(25): 8715-8724, 2000

6 alpha-Fluoro- and 6 alpha,9 alpha-difluoro-11 beta,21-dihydroxy-16 alpha,17 alpha-propylmethylenedioxypregn-4-ene-3,20-dione: synthesis and evaluation of activity and kinetics of their C-22 epimers. Steroids 63(1): 37-43, 1998

Rapid, regiospecific syntheses of deuterium substituted 6-(fluorine-18) fluorodopamine (alpha,alpha-D2',beta,beta-D2 and alpha,alpha,beta,beta-D-4) for mechanistic studies with positron emission tomography. Journal of Labelled Compounds and Radiopharmaceuticals 33(7): 645-654, 1993

Hydroxy steroids part 18 reactions of 17 beta chloro 16 alpha 17 alpha epoxy 5 alpha androstane and the preparation of 17 beta iodo 16 alpha 17 alpha epoxy 5 alpha androstane. Journal of the Chemical Society Perkin Transactions I (4): 486-492, 1972

Syntheses of (14 beta,15 beta,16 beta,17 alpha)- and (14 beta,15 alpha,16 alpha,17 alpha)-1,3,5(10)-estratriene-2,3,14,15,16,17- hexaols, possible candidates for the Inagami--Tamura endogenous digitalis-like factor, and their activity. Bioscience, Biotechnology, and Biochemistry 60(3): 405-410, 1996

Comparative structure of human neuronal alpha 2-alpha 7 and beta 2-beta 4 nicotinic acetylcholine receptor subunits and functional expression of the alpha 2, alpha 3, alpha 4, alpha 7, beta 2, and beta 4 subunits. Journal of Molecular Neuroscience 7(3): 217-228, 1996

Alpha,alpha-difluoro-gamma-iodo-gamma-trimethylsilyl ketones as precursors for the synthesis of alpha-substituted beta-fluoropyrroles. Tetrahedron Letters 36(29): 5119-5122, 1995

Synthetic studies on the construction of the fundamental skeleton of erythroxydiol part 10 syntheses of 3a 10a di methyl 3a beta 4a alpha 6a beta 10a alpha 10b beta per hydro cyclo propa j phenanthrene 5 8 dione and 8 alpha benzoyloxy 3a 10a dimethyl 3a beta 4a alpha 6a beta 10a alpha 10b beta per hydro cyclo propa j phenanthren 3 one. Journal of the Chemical Society Perkin Transactions I (23): 2581-2584, 1977

Oxidation of 5 beta-cholestane-3 alpha,7 alpha, 12 alpha-triol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid by cytochrome P-450(26) from rabbit liver mitochondria. Biochemical and Biophysical Research Communications 167(2): 391-395, 1990

Conversion of 5 beta-cholestane-3 alpha, 7 alpha, 12 alpha, 26-tetrol into 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestanoic acid by rabbit liver mitochondria. Biochemical and Biophysical Research Communications 153(1): 267-274, 1988

Sterol 27-hydroxylase in bile acid biosynthesis. Mechanism of oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid. Journal of Biological Chemistry 268(15): 11079-11085, 1993

Synthesis of the 1 beta hydroxylated bile acids and identification of 1 beta 3 alpha 7 alpha trihydroxy 5 beta cholan 24 oic acid and 1 beta 3 alpha 7 alpha 12 alpha tetrahydroxy 5 beta cholan 24 oic acid in human meconium. Chemical & Pharmaceutical Bulletin (Tokyo) 33(7): 3071-3073, 1985

Probes for narcotic receptor mediated phenomena. 18. Epimeric 6 alpha- and 6 beta-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5 alpha-epoxymorphinans as potential ligands for opioid receptor single photon emission computed tomography: synthesis, evaluation, and radiochemistry of [125I]-6 beta-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5 alpha-epoxymorphinan. Journal of Medicinal Chemistry 35(15): 2826-2835, 1992

Probes for narcotic receptor mediated phenomena 18. epimeric 6 alpha and 6 beta iodo 3 14 dihydroxy 17 cyclopropylmethyl 4 5 alpha epoxymorphinans as potential ligands for opioid receptor single photon emission computed tomography synthesis evaluation and radiochemistry of iodine 125 6 beta iodo 3 14 dihydroxy 17 cyclopropylmethyl 4 5 alpha epoxymorphinan. Journal of Medicinal Chemistry 35(15): 2826-2835, 1992