Condensed thiophenes and selenophenes: Thionyl chloride and selenium oxychloride as sulfur and selenium transfer reagents

被引:38
作者
Amaresh, RR [1 ]
Lakshmikantham, MV [1 ]
Baldwin, JW [1 ]
Cava, MP [1 ]
Metzger, RM [1 ]
Rogers, RD [1 ]
机构
[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA
关键词
D O I
10.1021/jo010858m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
3,4-Cyanomethyl substituted thiophenes reacted with thionyl chloride in the presence of base to give dicyano substituted thieno(3,4-c)thiophenes. The use of selenium oxychloride furnished the corresponding cyano substituted seleno(3,4-c)thiophene. 1,2-Phenylenediacetonitriles gave the corresponding cyano substituted benzo(c)thiophenes and benzo(c)selenenophenes, respectively, upon reaction with thionyl chloride and selenium oxychloride in the presence of base.
引用
收藏
页码:2453 / 2458
页数:6
相关论文
共 21 条
[1]   Thieno[3,4-c]thiophenes:: novel synthesis of 1,3-dicarbomethoxy-4,6-dicyanothieno[3,4-c]thiophene [J].
Amaresh, RR ;
Lakshmikantham, MV ;
Geng, RX ;
Cava, MP .
TETRAHEDRON LETTERS, 2000, 41 (46) :8843-8845
[2]   REACTIVE TETRAVALENT SULFUR INTERMEDIATES . A NONCLASSICAL THIOPHTHENE [J].
CAVA, MP ;
POLLACK, NM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (14) :3639-&
[3]   NONCLASSICAL CONDENSED THIOPHENES [J].
CAVA, MP ;
LAKSHMIKANTHAM, MV .
ACCOUNTS OF CHEMICAL RESEARCH, 1975, 8 (04) :139-144
[4]   TETRAPHENYLTHIENO[3,4-C]THIOPHENE . A STABLE NONCLASSICAL THIOPHENE [J].
CAVA, MP ;
HUSBANDS, GE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (14) :3952-&
[5]   NONCLASSICAL CONDENSED THIOPHENES .1. 1,3-DISUBSTITUTED THIENO[3,4-C]THIOPHENES [J].
CAVA, MP ;
POLLACK, NM ;
DIETERLE, GA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (08) :2558-2560
[6]  
CAVA MP, 1984, COMPREHENSIVE HETERO, V4, pCH3
[7]  
CAVA MP, 1973, J AM CHEM SOC, V95, P2651
[8]  
HARPP DN, 1987, PERSPECTIVES ORGANIC, P1
[9]  
HOFLE G, 1971, J AM CHEM SOC, V93, P6307
[10]   SYNTHESIS AND REACTIONS OF 1,3,4,6-TETRA-2-THIENYLTHIENO[3,4-C]THIOPHENE [J].
ISHII, A ;
NAKAYAMA, J ;
KAZAMI, J ;
IDA, Y ;
NAKAMURA, T ;
HOSHINO, M .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :78-82