Perfluoroalkylation of aliphatic thiols in the presence of sodium hydroxymethanesulfinate

被引：32

作者：

Anselmi, E ^{[1
]}

Blazejewski, JC ^{[1
]}

Tordeux, M ^{[1
]}

Wakselman, C ^{[1
]}

机构：

[1] Univ Versailles, SIRCOB, ESA CNRS 8086, F-78035 Versailles, France

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2000年 / 105卷 / 01期

关键词：

perfluoroalkyl sulfides; thiols; trifluoromethyl bromide; disulfides; hydroxymethanesulfinate;

D O I：

10.1016/S0022-1139(00)00286-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Direct perfluoroalkylation of aliphatic thiols was pet-formed in the presence of sodium hydroxymethanesulfinate (Rongalite). Reaction of mercaptoalkanoic esters with trifluoromethyl bromide gave the corresponding trifluoromethylthio ethers. Condensation of alkane dithiols with perfluoroalkyl iodides led mainly to fluorinated dithioethers. These alkylation reactions are interpreted as occurring via in situ formation of dialkyldisulfides. (C) 2000 Elsevier Science S.A. All rights reserved.

引用

页码：41 / 44

页数：4

共 14 条

[1] Synthetic uses of thio- and selenoesters of trifluoromethylated acids. 1. Preparation of trifluoromethyl sulfides and selenides [J].

Billard, T ;

Roques, N ;

Langlois, BR .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3813-3820

[2] ION-RADICAL PERFLUOROALKYLATION .11. PERFLUOROALKYLATION OF THIOLS BY PERFLUOROALKYL IODIDES IN THE ABSENCE OF INITIATORS [J].

BOIKO, VN ;

SHCHUPAK, GM .

JOURNAL OF FLUORINE CHEMISTRY, 1994, 69 (03) :207-212

[3]

CLARK JH, 1996, AROMATIC FLUORINATIO, P119

[4] REACTIONS OF BROMOTRIFLUOROMETHANE AND RELATED HALIDES .12. TRANSFORMATION OF DISULFIDES INTO PERFLUOROALKYL SULFIDES IN THE PRESENCE OF SULFOXYLATE ANION RADICAL PRECURSORS [J].

CLAVEL, JL ;

LANGLOIS, B ;

NANTERMET, R ;

TORDEUX, M ;

WAKSELMAN, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (24) :3371-3375

[5] NOVEL SYNTHESIS OF TRIFLUOROMETHYLTHIOACETIC ACID [J].

DEMARINIS, RM ;

BRYAN, WM .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (11) :2024-2025

[6] A SURVEY OF HAMMETT SUBSTITUENT CONSTANTS AND RESONANCE AND FIELD PARAMETERS [J].

HANSCH, C ;

LEO, A ;

TAFT, RW .

CHEMICAL REVIEWS, 1991, 91 (02) :165-195

[7] CHEMISTRY OF ALIPHATIC DISULFIDES .16. STUDIES ON ALKOXIDE CLEAVAGE OF 1,6-DIPHENYL-3,4-DITHIA-1,6-HEXANEDIONE [J].

HISKEY, RG ;

DENNIS, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (02) :563-&

[8] SULFENYLATION OF ORTHO-ESTERS - A NOVEL PREPARATION OF 2-[(TRIHALOMETHYL)THIO]ALKANOIC ACIDS [J].

MENDELSON, WL ;

LIU, JH ;

KILLMER, LB ;

LEVINSON, SH .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (03) :298-302

[9] SYNTHESIS OF NOVEL 3-(ALKYLTHIO)-2-HALOPYRIDINES AND RELATED DERIVATIVES [J].

PONTICELLO, GS ;

HARTMAN, RD ;

LUMMA, WC ;

BALDWIN, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (17) :3080-3082

[10] REACTIONS OF BROMOTRIFLUOROMETHANE AND RELATED HALIDES .8. CONDENSATIONS WITH DITHIONITE AND HYDROXYMETHANESULFINATE SALTS [J].

TORDEUX, M ;

LANGLOIS, B ;

WAKSELMAN, C .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (10) :2452-2453

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