Triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone as a new, selective and neutral system for the facile conversion of alcohols, thiols and selenols to alkyl halides in the presence of halide ions

被引：87

作者：

Iranpoor, N ^{[1
]}

Firouzabadi, H ^{[1
]}

Aghapour, G ^{[1
]}

Vaezzadeh, AR ^{[1
]}

机构：

[1] Shiraz Univ, Dept Chem, Coll Sci, Shiraz 71454, Iran

来源：

TETRAHEDRON | 2002年 / 58卷 / 43期

关键词：

quinones; triphenylphosphine; 2,3-dichloro-5,6-dicyanobenzoquinone;

D O I：

10.1016/S0040-4020(02)01089-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mixture of triphenylphosphine (Ph3P) and 2,3-dichloro-5,6-dicyanobenzoquinone in CH2Cl2 affords a complex which in the presence of R4NX (X = Cl, Br, I) converts alcohols, thiols and selenols into their corresponding alkyl halides in high yields at room temperature. The method is highly selective for the conversion of 1degrees alcohols in the presence of 2degrees ones and also V and 2degrees alcohols in the presence of 3degrees alcohols, thiols, epoxides, trimethylsilyl- and tetrahydropyranyl ethers, 1,3 dithianes, disulfides, and amides. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：8689 / 8693

页数：5

共 27 条

[1] AROMATIC MOLECULAR CMPLEXES OF THE ELECTRON DONOR-ACCEPTOR TYPE
ANDREWS, LJ
[J]. CHEMICAL REVIEWS, 1954, 54 (05) : 713 - 776
[2] Ball D H, 1968, Adv Carbohydr Chem Biochem, V23, P233
[3] Ball D H, 1969, Adv Carbohydr Chem Biochem, V24, P139
[4] QUINONE DEHYDROGENATION - OXIDATION OF BENZYLIC ALCOHOLS WITH 2,3-DICHLORO-5,6-DICYANOBENZOQUINONE
BECKER, HD
BJORK, A
ADLER, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (09) : 1596 - 1600
[5] BOSE AK, 1973, TETRAHEDRON LETT, P3937
[6] Dagani M.J., 1971, US Patent, Patent No. 3624159
[7] The constitution of some additive compounds of tertiary phosphines.
Davies, WC
Walters, WP
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1935, : 1786 - 1792
[8] Foster, 1955, ORG SYN COLLECTIVE, VIII, P771
[9] HARISON CR, 1983, J ORG CHEM, V48, P3721
[10] Harrison G. C., 1953, ORG SYNTH COLL, VIII, P370

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