THE VINYLATION OF ARENES WITH 1-(PHENYLTHIO)VINYLSTANNANES

被引:8
作者
TAKEDA, T
KANAMORI, F
MASUDA, M
FUJIWARA, T
机构
[1] Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo
关键词
D O I
10.1016/0040-4039(91)80085-K
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The vinylation of arenes using 1-(phenylthio)vinylstannanes proceeded in the presence of tin(IV) chloride and molecular sieves 4A to afford 1-arylalkenyl sulfides in good yields. The stereochemistry of the olefinic moiety was determined after oxidation to the corresponding sulfones and it was found that the present reaction gave the thermodynamically stable stereoisomers.
引用
收藏
页码:5567 / 5570
页数:4
相关论文
共 10 条
[1]   GENERATION OF AND OLEFINATION WITH ALPHA-S-PERHETEROSUBSTITUTED, ALPHA-S-PERHETEROSUBSTITUTED, ALPHA-SE-PERHETEROSUBSTITUTED, AND ALPHA-SN-PERHETERO-SUBSTITUTED (TRIMETHYLSILYL)-METHYLLITHIUM DERIVATIVES [J].
GROBEL, BT ;
SEEBACH, D .
CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (03) :852-866
[2]  
JACKMAN LM, 1969, APPLICATIONS NUCLEAR, P184
[3]   PHOTOLYSIS OF VINYL HALIDES - PREFERENTIAL FORMATION OF VINYL CATIONS BY COPPER(II) SALTS [J].
KITAMURA, T ;
KOBAYASHI, S ;
TANIGUCHI, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (10) :2641-2645
[4]  
OCHIAI M, 1986, J CHEM SOC CHEM COMM, P1383
[5]   NUCLEOPHILIC VINYLIC SUBSTITUTION - A SINGLE-STEP OR A MULTISTEP PROCESS [J].
RAPPOPORT, Z .
ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (01) :7-15
[6]   PREPARATION AND CHEMISTRY OF VINYL TRIFLATES .16. MECHANISM OF ALKYLATION OF AROMATIC SUBSTRATES [J].
STANG, PJ ;
ANDERSON, AG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (05) :1520-1525
[7]   GAMMA-(PHENYLTHIO)ALLYL AND ALLENYLSTANNANES AS UNSATURATED THIONIUM ION EQUIVALENTS [J].
TAKEDA, T ;
NAKAYAMA, A ;
FURUKAWA, T ;
FUJIWARA, T .
TETRAHEDRON LETTERS, 1990, 31 (46) :6685-6688
[8]   PREPARATION AND REACTION OF 1-(METHYLTHIOVINYLLITHIUM AND PHENYLTHIO-VINYLLITHIUM REAGENTS [J].
TAKEDA, T ;
FURUKAWA, H ;
FUJIMORI, M ;
SUZUKI, K ;
FUJIWARA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (07) :1863-1869
[9]   ENOL THIOETHERS AS ENOL SUBSTITUTES - AN ALKYLATION SEQUENCE [J].
TROST, BM ;
LAVOIE, AC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (15) :5075-5090
[10]   COUPLING REACTION OF ALLYLSTANNANES WITH ARENES [J].
YAMAGUCHI, J ;
TAKAGI, Y ;
NAKAYAMA, A ;
FUJIWARA, T ;
TAKEDA, T .
CHEMISTRY LETTERS, 1991, (01) :133-136