GENERATION AND REARRANGEMENT OF C2-SYMMETRICAL CHIRAL ALLYL ANIONS DERIVED FROM DIBENZO-2,2'-DITHIOPROPENES AND 1,1'-DINAPHTHO-2,2'-DITHIOPROPENES

被引:6
作者
DORE, A
COSSU, S
DELUCCHI, O
VALLE, G
机构
[1] UNIV SASSARI,DIPARTMENTO CHIM,VIA VIENNA 2,I-07100 SASSARI,ITALY
[2] CNR,CTR BIOPOLIMERI,I-35131 PADUA,ITALY
关键词
1,3-DITHIOALLYL ANIONS; DIBENZO-2,2'-DITHIOL; 1,1'-DINAPHTHO-2,2'-DITHIOL; ATROPISOMERIC SULFUR REAGENTS; C2-SYMMETRICAL CHIRAL REAGENTS;
D O I
10.1016/S0040-4039(00)92304-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The allyl anions generated from 4H-dinaphtho[2,1-f:1',2'-h][1,5]dithionin (6) and 2-ethenyl-dinaphtho[2,1-d:1',2'-f][1,3]dithiepin (8) rearranged both to the thiolate 10 which further reacted with water or methyl iodide to afford 9 or 12 respectively. A similar behavior was exhibited by the anion of 4H-dibenzo[fh][1,5]dithionin (15).
引用
收藏
页码:4771 / 4774
页数:4
相关论文
共 11 条
[1]   PREPARATIVE METHODS FOR BETA-ACYL VINYL ANION EQUIVALENTS FROM ENONES OR ALLYL SULFIDES [J].
COHEN, T ;
BENNETT, DA ;
MURA, AJ .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (14) :2506-2507
[2]   NEW SYNTHESIS OF ALPHA,BETA-UNSATURATED ALDEHYDES USING 1,3-BIS(METHYLTHIO)ALLYLLITHIUM [J].
COREY, EJ ;
ERICKSON, BW ;
NOYORI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (07) :1724-&
[3]  
COREY EJ, 1970, TETRAHEDRON LETT, P311
[4]  
COSSU S, 1990, HETEROATOM CHEMISTRY /, P143
[5]  
de Lucchi O, 2004, ORG REACTIONS, V40, P157
[6]   ATROPISOMERIC SULFUR-COMPOUNDS IN ORGANIC-SYNTHESIS - GENERATION AND REACTIONS OF THE CARBANIONS OF DINAPHTHO[2,1-D-1',2'-F][1,3]DITHIEPINE AND ITS OXIDES [J].
DELOGU, G ;
DELUCCHI, O ;
LICINI, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (07) :411-412
[7]   SYNTHESIS AND LITHIATION OF GAMMA,GAMMA-DIFUNCTIONALIZED KETENE DITHIOACETALS - ACCESS TO A NEW SYNTHETIC EQUIVALENT OF A BETA-HYDROXY-BETA-LITHIOACRYLATE - X-RAY MOLECULAR-STRUCTURE OF 2-(1,3-DITHIAN-2-YLIDENEMETHYL)-1,3-DITHIANE [J].
DZIADULEWICZ, E ;
GILES, M ;
MOSS, WO ;
GALLAGHER, T ;
HARMAN, M ;
HURSTHOUSE, MB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (10) :1793-1798
[8]   SYNTHESIS AND REACTIVITY OF LITHIATED GAMMA-FUNCTIONALIZED KETENE DITHIOACETALS - GENERATION OF A FLEXIBLE BETA-LITHIOACRYLATE EQUIVALENT [J].
DZIADULEWICZ, E ;
HODGSON, D ;
GALLAGHER, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12) :3367-3373
[9]  
FANG JM, 1990, SYNLETT, P285
[10]  
MURATA I, 1975, TETRAHEDRON LETT, P1895