Sulfonyl esters .7. The second and third sequences in the trithioorthoformate reaction

被引:3
作者
Ginige, KA [1 ]
Goehl, JE [1 ]
Langler, RF [1 ]
机构
[1] MT ALLISON UNIV,DEPT CHEM,SACKVILLE,NB E0A 3C0,CANADA
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1996年 / 74卷 / 09期
关键词
single electron transfer; sulfonate esters; sulfenes;
D O I
10.1139/v96-181
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A previous report has established the intermediacy of a sulfide-sulfonate ester in the one-pot conversion of an aryl mercaptan and a sulfonate ester into the corresponding trithioorthoformate. This report describes evidence for the sequential intermediacy of a bissulfide-sulfonate ester and a dithiosulfene in the conversion of the sulfide-sulfonate ester into the trithioorthoformate. A new sulfonate ester is shown to give the highest yield of trithioorthoformate.
引用
收藏
页码:1638 / 1648
页数:11
相关论文
共 30 条
[1]   A SULFENE UMPOLUNG [J].
ALLMANN, R ;
HANEFELD, W ;
KRESTEL, M ;
SPANGENBERG, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (11) :1133-1134
[2]   SULFONYL ESTERS .2. CS-CLEAVAGE IN SOME SUBSTITUTION-REACTIONS OF NITROBENZENESULFONATES [J].
BAUM, JC ;
BOLHASSAN, J ;
LANGLER, RF ;
PUJOL, PJ ;
RAHEJA, RK .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (08) :1450-1455
[3]   SULFONYL ESTERS .6. ELUCIDATION OF THE FIRST SEQUENCE IN THE TRITHIOORTHOFORMATE REACTION [J].
BAUM, JC ;
BLACK, BE ;
PRECEDO, L ;
GOEHL, JE ;
LANGLER, RF .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1995, 73 (03) :444-452
[4]   SULFONYL ESTERS .3. THE FORMATION OF SULFONE-SULFONATES IN THE REACTIONS OF ARYL METHANESULFONATES WITH SODIUM HYDRIDE [J].
BAUM, JC ;
DURKIN, KA ;
PRECEDO, L ;
OBLENES, SB ;
GOEHL, JE ;
LANGLER, RF ;
MACCORMACK, GK ;
SMITH, LL .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1991, 69 (12) :2127-2135
[5]  
BAX PC, 1970, RECL TRAV CHIM PAY-B, V89, P265
[6]   EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].
BORDWELL, FG .
ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463
[7]   The reversibility of the rearrangement of o-hydroxy-sulphones [J].
Coats, RR ;
Gibson, DT .
JOURNAL OF THE CHEMICAL SOCIETY, 1940, :442-446
[8]   ELIMINATION - ADDITION MECHANISMS OF ACYL GROUP TRANSFER - HYDROLYSIS AND AMINOLYSIS OF ARYL PHENYLMETHANESULFONATES [J].
DAVY, MB ;
DOUGLAS, KT ;
LORAN, JS ;
STELTNER, A ;
WILLIAMS, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (04) :1196-1206
[9]   SULFONYL ESTERS-1 - THE REDUCTION OF TRIBROMOPHENYL SULFONATES WITH MERCAPTIDE ANIONS [J].
DURKIN, KA ;
LANGLER, RF ;
MORRISON, NA .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (12) :3070-3076
[10]   SULFOHALOFORM REACTION - STEPWISE CONVERSION OF DIALKYL SULFIDES INTO ALKANESULFONYL CHLORIDES [J].
GROSSERT, JS ;
LANGLER, RF .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (03) :407-420