PHENYLIODINE(III) BIS(TRIFLUOROACETATE) AS A RADICAL-CATION GENERATING REAGENT

被引：33

作者：

EBERSON, L ^{[1
]}

HARTSHORN, MP ^{[1
]}

PERSSON, O ^{[1
]}

机构：

[1] UNIV CHRISTCHURCH,DEPT CHEM,CHRISTCHURCH,NEW ZEALAND

来源：

ACTA CHEMICA SCANDINAVICA | 1995年 / 49卷 / 09期

关键词：

D O I：

10.3891/acta.chem.scand.49-0640

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The use of phenyliodine(III) bis(trifluoroacetate) (PIFA) as a one-electron oxidant For aromatic compounds has been explored. In trifluoroacetic acid or 1,1,1,3,3,3-hexafluoro-2-propanol, a number of radical cations were generated in the temperature range -10 to 20 degrees C and structurally assigned by EPR spectroscopy. The oxidative power of PIFA was found to be similar to that of thallium(III) trifluoroacetate under the conditions employed. Thus PIFA oxidation is a useful, less toxic complement to existing methods of radical cation generation. 1,1,1,3,3,3-Hexafluoro-2-propanol was found to be an excellent solvent for radical cations. The use of PIFA in 'inverted spin trapping' with alpha-phenyl-N-tert-butylnitrone (PEN) was investigated briefly, and it was found that it sustains this reaction with nucleophiles such as fluoride, chloride and acetate ion, tetramethylsuccinimide anion and benzotriazolate anion.

引用

页码：640 / 644

页数：5

共 50 条

[21] Non-phenolic oxidative coupling of phenol ether derivatives using phenyliodine(III) bis(trifluoroacetate)
Kita, Y
Gyoten, M
Ohtsubo, M
Tohma, H
Takada, T
[J]. CHEMICAL COMMUNICATIONS, 1996, (12) : 1481 - 1482
[22] Oxidative rearrangement of pentaalkoxychalcones with phenyliodine(III) bis(trifluoroacetate) (PIFA):: synthesis of (±)-10-bromopterocarpin and (±)-pterocarpin
Miki, Y
Fujita, R
Matsushita, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (16): : 2533 - 2536
[23] Regioselective bipyrrole coupling of pyrroles and 3-substituted pyrroles using phenyliodine(III) bis(trifluoroacetate)
Dohi, Toshifumi
Morimoto, Koji
Ito, Motoki
Kita, Yasuyuki
[J]. SYNTHESIS-STUTTGART, 2007, (18): : 2913 - 2919
[24] REFLECTANCE SPECTRA OF BIS-FUSED TTF RADICAL-CATION SALTS
TAJIMA, H
ARIFUKU, M
OHTA, T
MORI, T
MISAKI, Y
YAMABE, T
MORI, H
TANAKA, S
[J]. SYNTHETIC METALS, 1995, 71 (1-3) : 1951 - 1952
[25] STRUCTURE OF THE TOLUENE RADICAL-CATION
NENDEL, M
TOLBERT, LM
HOUK, KN
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 72 - COMP
[26] STABLE RADICAL-CATION OF HYDROCARBON
HUNIG, S
FRIEDRICH, HJ
SCHEUTZOW, D
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1964, 3 (10) : 701 - &
[27] THE FIRST SPECTROSCOPIC IDENTIFICATION OF AN ENOL RADICAL-CATION IN SOLUTION - THE ANISYL-DIMESITYLETHENOL RADICAL-CATION
SCHMITTEL, M
GESCHEIDT, G
ROCK, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (19): : 1961 - 1963
[28] Chemoselective arylsulfenylation of 2-aminoimidazo[1,2-a]pyridines by phenyliodine(III) bis(trifluoroacetate) (PIFA)
Hamdouchi, C
Sanchez, C
Ezquerra, J
[J]. SYNTHESIS-STUTTGART, 1998, (06): : 867 - 872
[29] Phenyliodine(III) bis(trifluoroacetate) mediated synthesis of phenanthro[9,10-d] fused isoxazoles and pyrimidines
Olivera, R
SanMartin, R
Pascual, S
Herrero, M
Domínguez, E
[J]. TETRAHEDRON LETTERS, 1999, 40 (17) : 3479 - 3480
[30] A metal-free approach to the synthesis of indoline derivatives by a phenyliodine(III) bis(trifluoroacetate)-mediated amidohydroxylation reaction
Correa, Arkaitz
Tellitu, Imanol
Dominguez, Esther
SanMartin, Raul
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (21): : 8316 - 8319

← 1 2 3 4 5 →