Addition of hydrogen halides to acetylenic selenides. Synthesis of 1-halo-1-selenoalkenes

被引:81
作者
Comasseto, JV
Menezes, PH
Stefani, HA
Zeni, G
Braga, AL
机构
[1] UNIV SAO PAULO,IQ,BR-05508 SAO PAULO,SP,BRAZIL
[2] UNIV SAO PAULO,FCF,BR-05508 SAO PAULO,SP,BRAZIL
[3] UNIV FED SANTA MARIA,DQ,SANTA MARIA,RS,BRAZIL
关键词
D O I
10.1016/0040-4020(96)00505-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acetylenic selenides react with HX (X=Cl, Br, I) at room temperature to give 1-halo-1-selenoalkenes in good yields. The 1-iodo-1-selenoalkenes were transformed into the corresponding vinylic organometallics (M=Zn, Cu, Cr). Copyright (C) 1996 Elsevier Science Ltd.
引用
收藏
页码:9687 / 9702
页数:16
相关论文
共 26 条
[11]  
COUTROT C, 1987, SYNTHESIS-STUTTGART, P169
[12]   STABILITY AND STRUCTURE OF SELENIUM STABILIZED CARBENIUM IONS [J].
HEVESI, L .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1992, 67 (1-4) :155-168
[13]   PREPARATION AND REACTIONS OF POLYFUNCTIONAL ORGANOZINC REAGENTS IN ORGANIC-SYNTHESIS [J].
KNOCHEL, P ;
SINGER, RD .
CHEMICAL REVIEWS, 1993, 93 (06) :2117-2188
[14]   PREPARATION AND REACTIVITY OF FUNCTIONALIZED ALKENYL-ZINC, ALKENYL-COPPER, AND ALKENYL-CHROMIUM ORGANOMETALLICS [J].
KNOCHEL, P ;
RAO, CJ .
TETRAHEDRON, 1993, 49 (01) :29-48
[15]   SURFACE-MEDIATED REACTIONS .1. HYDROHALOGENATION OF ALKENES AND ALKYNES [J].
KROPP, PJ ;
DAUS, KA ;
CRAWFORD, SD ;
TUBERGEN, MW ;
KEPLER, KD ;
CRAIG, SL ;
WILSON, VP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (20) :7433-7434
[16]   SURFACE-MEDIATED REACTIONS .4. HYDROHALOGENATION OF ALKYNES [J].
KROPP, PJ ;
CRAWFORD, SD .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3102-3112
[17]  
LIPSHUTZ BH, 1992, ORG REACTIONS, V41, P135, DOI [DOI 10.1002/0471264180.0R041.02, 10.1002/0471264180.or041.02]
[18]  
PERRIN DD, 1966, PURIFICATION LABORAT
[19]  
Radchenko S.I., 1989, RUSS CHEM REV+, V58, P948, DOI [10.1070/RC1989v058n10ABEH003488, DOI 10.1070/RC1989V058N10ABEH003488]
[20]  
RIEKE RD, 1992, J AM CHEM SOC, V114, P5110