The selective functionalization of saturated hydrocarbons. Part 42. Further studies in selective phenylselenation.

被引：3

作者：

Barton, DHR ^{[1
]}

Lalic, G ^{[1
]}

Smith, JA ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77843 USA

来源：

TETRAHEDRON | 1998年 / 54卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(97)10397-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved procedure for the phenylselenation of saturated hydrocarbons has been developed. The reaction of tributylphosphine with diphenyl diselenide in the presence of Fe-II picolinate in pyridine-acetonitrile-trace of water affords a quantitative yield of phenylselenol. Subsequent or prior addition of the saturated hydrocarbon and final addition of 30% hydrogen peroxide gives phenylselenation in excellent yield based on the oxidant added. The mechanism of this reaction has been further studied; carbon and hydroxyl radicals are not part of the mechanism. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1725 / 1734

页数：10

共 25 条

[1] BALAVOINE G, 1989, NEW J CHEM, V13, P691
[2] FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .10. A COMPARATIVE-STUDY OF CHEMICAL AND ELECTROCHEMICAL PROCESSES (GIF AND GIF-ORSAY SYSTEMS) IN PYRIDINE, IN ACETONE AND IN PYRIDINE-CO-SOLVENT MIXTURES
BALAVOINE, G
BARTON, DHR
BOIVIN, J
GREF, A
LECOUPANEC, P
OZBALIK, N
PESTANA, JAX
RIVIERE, H
[J]. TETRAHEDRON, 1988, 44 (04) : 1091 - 1106
[3] DIRECT CONVERSION OF SATURATED-HYDROCARBONS INTO PHENYLSELENO DERIVATIVES
BARTON, DHR
BOIVIN, J
LECOUPANEC, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (18) : 1379 - 1381
[4] N-hydroxypyridine-2(1H)-thione derivatives of carboxylic acids as activated esters .2. Applications in peptide synthesis.
Barton, DHR
Ferreira, JA
[J]. TETRAHEDRON, 1996, 52 (28) : 9367 - 9386
[5] THE FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .20. ALKYL HYDROPEROXIDES - REACTION INTERMEDIATES IN THE OXIDATION OF SATURATED-HYDROCARBONS BY GIF-TYPE REACTIONS AND MECHANISTIC STUDIES ON THEIR FORMATION
BARTON, DHR
BEVIERE, SD
CHAVASIRI, W
CSUHAI, E
DOLLER, D
LIU, WG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (06) : 2147 - 2156
[6] FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .14. FURTHER-STUDIES ON THE MECHANISM OF GIF-TYPE SYSTEMS
BARTON, DHR
HALLEY, F
OZBALIK, N
SCHMITT, M
YOUNG, E
BALAVOINE, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (18) : 7144 - 7149
[7] ELECTROPHILIC FLUORINATION OF SOME STEROIDAL ALPHA,BETA-UNSATURATED KETONES
BARTON, DHR
LISTERJAMES, J
HESSE, RH
PECHET, MM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (04): : 1105 - 1110
[8] FUNCTIONALIZATION OF SATURATED-HYDROCARBONS .1. SOME REACTIONS OF A FERROUS CHLORIDE CHLORAMINE-T COMPLEX WITH HYDROCARBONS
BARTON, DHR
HAYMOTHERWELL, RS
MOTHERWELL, WB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (02): : 445 - 451
[9] THE ROLE OF ORGANIC TELLURIDES AS ACCUMULATORS AND EXCHANGERS OF CARBON RADICALS
BARTON, DHR
OZBALIK, N
SARMA, JC
[J]. TETRAHEDRON LETTERS, 1988, 29 (50) : 6581 - 6584
[10] The selective functionalization of saturated hydrocarbons .32. Distinction between the Fe-II-Fe-IV and Fe-III-Fe-V manifolds in Gif chemistry. The importance of carboxylic acids for alkane activation. Evidence for a dimeric iron species involved in Gif-type chemistry
Barton, DHR
Hu, B
Taylor, DK
Wahl, RUR
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (06): : 1031 - 1041

← 1 2 3 →