SUBSTITUTION-REACTIONS OF 3-SULFOLENYL CARBANIONS

被引:30
作者
CHOU, TS [1 ]
CHOU, SSP [1 ]
机构
[1] FU JEN CATHOLIC UNIV,DEPT CHEM,TAIPEI,TAIWAN
关键词
3-SULFOLENES; 3-SULFOLENYL ANIONS; SUBSTITUTION REACTIONS; SUBSTITUTED 1,3-BUTADIENES; CHELETROPIC REACTIONS;
D O I
10.1002/jccs.199200097
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
3-Sulfolenes are easily converted to the corresponding 1,3-dienes by cheletropic removal of SO2. In addition, the generation of 3-sulfolenyl anions are achieved under several reaction conditions. Therefore, 3-sulfolenes serve as butadienyl anion equivalents and this stragegy has been applied to the preparations of substituted dienes and the total synthesis of natural products.
引用
收藏
页码:625 / 633
页数:9
相关论文
共 92 条
[1]  
AKOPYAN AN, 1962, ZH OBSHCH KHIM+, V32, P2443
[2]   CYCLIC DIENES .3. THE SYNTHESIS OF THIOPHENE 1-DIOXIDE [J].
BAILEY, WJ ;
CUMMINS, EW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (07) :1932-1936
[3]  
BERESTOVITSKAYA VM, 1979, ZH ORG KHIM+, V15, P185
[4]   ISOPRENE FUNCTIONALIZATION - E-Z-ISOMERISM OF 1-SULFONYL SUBSTITUTED 2-METHYLBUTADIENES [J].
BURGER, JJ ;
CHEN, TBRA ;
WAARD, ERD ;
HUISMAN, HO .
TETRAHEDRON, 1980, 36 (06) :723-726
[5]  
CHABARDES P, 1973, Patent No. 2319518
[6]  
CHOU SSP, 1990, SYNTHESIS-STUTTGART, P219, DOI 10.1055/s-1990-26836
[7]   INTRAMOLECULAR DIELS-ALDER REACTIONS VIA 3-(PHENYLTHIO)-4-(TRIMETHYLSILYL)-3-SULFOLENE [J].
CHOU, SSP ;
LEE, CM .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1991, 38 (05) :491-496
[8]   A FACILE SYNTHESIS OF STABLE PRECURSORS TO 2-ALKYLATED AND 2,3-DIALKYLATED 1,3-BUTADIENES [J].
CHOU, SSP ;
SUN, CM .
TETRAHEDRON LETTERS, 1990, 31 (07) :1035-1038
[9]   SPIRODIALKYLATION OF 3-(PHENYLTHIO)-3-SULFOLENE AND SUBSEQUENT SYNTHETIC TRANSFORMATIONS [J].
CHOU, SSP ;
SUNG, CC .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1989, 36 (06) :601-607
[10]   2-ACETYL-3-(PHENYLTHIO)-1,3-BUTADIENE - A NOVEL DIELS-ALDER DIENE AND DIENOPHILE [J].
CHOU, SSP ;
TSAI, CY .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (22) :5305-5308