NUCLEOPHILIC VINYLIC SUBSTITUTIONS OF (Z)-(BETA-(PHENYLSULFONYL)ALKENYL)IODONIUM TETRAFLUOROBORATES WITH TETRABUTYLAMMONIUM HALIDES - RETENTION OF CONFIGURATION

被引:40
作者
OCHIAI, M
OSHIMA, K
MASAKI, Y
机构
[1] Gifu Pharmaceutical University, Gifu, 502
关键词
D O I
10.1016/0040-4039(91)80572-N
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nucleophilic vinylic substitutions of (Z)-(beta-(phenylsulfonyl)alkenyl)-phenyliodonium tetrafluoroborates 1 with tetrabutylammonium halides (Cl, Br, and I) proceed with exclusive retention of configuration at room temperature and afford (Z)-beta-(phenylsulfonyl)vinyl halides 2 in high yields.
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收藏
页码:7711 / 7714
页数:4
相关论文
共 10 条
[1]   IMPORTANCE OF HYPERCONJUGATION IN NUCLEOPHILIC VINYLIC SUBSTITUTION [J].
APELOIG, Y ;
RAPPOPORT, Z .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :5095-5098
[2]   STEREOSELECTION IN NUCLEOPHILIC-SUBSTITUTION AT AN SP2 CARBON [J].
MILLER, SI .
TETRAHEDRON, 1977, 33 (10) :1211-1218
[3]   REACTIONS OF NUCLEOPHILES WITH ETHYLENIC SUBSTRATES [J].
MODENA, G .
ACCOUNTS OF CHEMICAL RESEARCH, 1971, 4 (02) :73-&
[4]   LIGAND-COUPLING REACTIONS OF HYPERVALENT SPECIES [J].
OAE, S ;
UCHIDA, Y .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (07) :202-208
[5]   INVERSION OF CONFIGURATION IN NUCLEOPHILIC VINYLIC SUBSTITUTIONS OF (E)-BETA-ALKYLVINYLIODONIUM TETRAFLUOROBORATES WITH HALIDES [J].
OCHIAI, M ;
OSHIMA, K ;
MASAKI, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (18) :7059-7061
[6]   GENERATION OF [BETA-(PHENYLSULFONYL)ALKYLIDENE]CARBENES FROM HYPERVALENT ALKENYLIODONIUM AND ALKYNYLIODONIUM TETRAFLUOROBORATES AND SYNTHESIS OF 1-(PHENYLSULFONYL)CYCLOPENTENES [J].
OCHIAI, M ;
KUNISHIMA, M ;
TANI, S ;
NAGAO, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) :3135-3142
[7]  
RAPPOPORT Z, 1985, RECL TRAV CHIM PAY B, V104, P309
[8]   NUCLEOPHILIC VINYLIC SUBSTITUTION - A SINGLE-STEP OR A MULTISTEP PROCESS [J].
RAPPOPORT, Z .
ACCOUNTS OF CHEMICAL RESEARCH, 1981, 14 (01) :7-15
[9]  
Rappoport Z., 1969, ADV PHYS ORG CHEM, V7, P1
[10]  
SHAINYAN BA, 1986, USP KHIM, V55, P942