Montmorillonite K 10-catalyzed regioselective addition of thiols and thiobenzoic acids onto olefins: an efficient synthesis of dithiocarboxylic esters

被引:95
作者
Kanagasabapathy, S
Sudalai, A
Benicewicz, BC [1 ]
机构
[1] Rensselaer Polytech Inst, NYS Ctr Polymer Synth, Troy, NY 12180 USA
[2] Rensselaer Polytech Inst, Dept Chem, Troy, NY 12180 USA
关键词
addition reactions; alkenes; thiols; clays; sulfur compounds; chain-transfer agents; living-radical polymerization; reversible addition-fragmentation chain-transfer polymerization;
D O I
10.1016/S0040-4039(01)00570-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The addition of thiols and thiobenzoic acids onto olefins: proceeded regioselectively in a Markovnikov manner in the presence of Montmorillonite K 10 (Mont K 10) clay as the catalyst to afford thioethers and thiocarboxylic S-esters, while high selectivity to anti-Markovnikov products: was realized in the absence of any catalyst. Treatment of the esters with Lawesson's reagent provided the corresponding dithiocarboxylic esters in high yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3791 / 3794
页数:4
相关论文
共 20 条
[1]   ADDITION OF THIOLS TO STYRENES - FORMATION OF BENZYLIC THIOETHERS [J].
BELLEY, M ;
ZAMBONI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (05) :1230-1232
[2]   BETA-DIMETHYLAMINOETHYL ESTERS OF ORGANIC DITHIO ACIDS .2. ESTERS OF AROMATIC DITHIO ACIDS [J].
BOST, RW ;
SHEALY, OL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (01) :25-28
[3]   A more versatile route to block copolymers and other polymers of complex architecture by living radical polymerization: The RAFT process [J].
Chong, YK ;
Le, TPT ;
Moad, G ;
Rizzardo, E ;
Thang, SH .
MACROMOLECULES, 1999, 32 (06) :2071-2074
[4]  
Curran D. P., 1991, COMPREHENSIVE ORGANI, V4, P715
[5]  
DAVY H, 1985, CHEM IND-LONDON, P824
[6]  
De Brouwer H, 2000, J POLYM SCI POL CHEM, V38, P3596, DOI 10.1002/1099-0518(20001001)38:19<3596::AID-POLA150>3.0.CO
[7]  
2-F
[9]   Reaction of aliphatic olefins with thiophenol [J].
Ipatieff, VN ;
Pines, H ;
Friedman, BS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1938, 60 :2731-2734
[10]  
Kumar P, 1999, SYNLETT, P1921