Preparation of cyclic disulfides from bisthiocyanates

被引:36
作者
Burns, CJ
Field, LD [1 ]
Morgan, J
Ridley, DD
Vignevich, V
机构
[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia
[2] Univ Sydney, Cooperat Res Ctr Mol Engn & Technol, Sydney, NSW 2006, Australia
关键词
thiocyanates; disulfides; sulfur compounds;
D O I
10.1016/S0040-4039(99)01333-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild method for the preparation of disulfides from acyclic bisthiocyanates is presented. The method involves cleavage of thiocyanates with TBAF to form. the cyclic disulfides in moderate to good yield. The method can also be applied to the synthesis of acyclic disulfides. Base-sensitive functionalities, such as esters, are unaffected by the reaction conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6489 / 6492
页数:4
相关论文
共 36 条
[1]  
Affleck JG., 1950, J ORG CHEM, V15, P865
[2]  
[Anonymous], CHEM THIOL GROUP 2
[3]  
Backer HJ, 1938, RECL TRAV CHIM PAY-B, V57, P1183
[4]   COMPARISON OF ORGANIC MONOLAYERS ON POLYCRYSTALLINE GOLD SPONTANEOUSLY ASSEMBLED FROM SOLUTIONS CONTAINING DIALKYL DISULFIDES OR ALKENETHIOLS [J].
BIEBUYCK, HA ;
BIAN, CD ;
WHITESIDES, GM .
LANGMUIR, 1994, 10 (06) :1825-1831
[5]   A new simple access to trifluoromethyl thioethers or selenoethers from trifluoromethyl trimethylsilane and disulfides or diselenides [J].
Billard, T ;
Langlois, BR .
TETRAHEDRON LETTERS, 1996, 37 (38) :6865-6868
[6]  
BRINTZINGER H, 1954, BER, V87, P314
[7]   BORON-TRIFLUORIDE CATALYZED ADDITION OF DISULFIDES TO ALKENES [J].
CASERIO, MC ;
FISHER, CL ;
KIM, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (22) :4390-4393
[8]   DITHIOTHREITOL NEW PROTECTIVE REAGENT FOR SH GROUPS [J].
CLELAND, WW .
BIOCHEMISTRY, 1964, 3 (04) :480-&
[9]   A biosensor that uses ion-channel switches [J].
Cornell, BA ;
BraachMaksvytis, VLB ;
King, LG ;
Osman, PDJ ;
Raguse, B ;
Wieczorek, L ;
Pace, RJ .
NATURE, 1997, 387 (6633) :580-583
[10]  
CRAGG RH, 1973, TETRAHEDRON LETT, V14, P655