Hydroselenation of alkynes by lithium butylselenolate: An approach in the synthesis of vinylic selenides

被引:77
作者
Zeni, G [1 ]
Stracke, MP
Nogueira, CW
Braga, AL
Menezes, PH
Stefani, HA
机构
[1] Univ Fed Santa Maria, CCNE, Lab Sintese Reatividade Avaliacao Toxicol & Farma, BR-97105900 Santa Maria, RS, Brazil
[2] Univ Fed Pernambuco, Dept Quim Fundamental, Recife, PE, Brazil
[3] Univ Sao Paulo, Fac Ciencias Farmaceut, Sao Paulo, Brazil
关键词
D O I
10.1021/ol0498904
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Vinylic selenides were prepared in good yields by hydroselenation of alkynes with lithium butylselenolate generated by reaction of n-butyllithium with elemental selenium. The regio- and stereochernistry of the hydroselenation depend on the nature of the substituents bonded to the alkyne.
引用
收藏
页码:1135 / 1138
页数:4
相关论文
共 20 条
[1]  
Back T. G., 1999, ORGANOSELENIUM CHEM
[2]  
Barros OSD, 2002, TETRAHEDRON LETT, V43, P7921
[3]   STEREOSELECTIVE SYNTHESIS OF VINYLIC SELENIDES [J].
COMASSETO, JV ;
FERREIRA, JTB .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 216 (03) :287-294
[4]   Vinylic selenides and tellurides - Preparation, reactivity and synthetic applications [J].
Comasseto, JV ;
Ling, LW ;
Petragnani, N ;
Stefani, HA .
SYNTHESIS-STUTTGART, 1997, (04) :373-&
[5]   VINYLIC SELENIDES [J].
COMASSETO, JV .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1983, 253 (02) :131-181
[6]  
DADBOUB MJ, 2001, TETRAHEDRON, V57, P4271
[7]  
DADBOUB MJ, 2001, TETRAHEDRON LETT, V42, P1595
[8]  
DADBOUB MJ, 1996, TETRAHEDRON LETT, V37, P9005
[9]   ELECTROPHILIC ADDITION OF BENZENESELENEYL CHLORIDE TO HYDROXYALKYNES [J].
FILER, CN ;
AHERN, D ;
FAZIO, R ;
SHELTON, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (07) :1313-1315
[10]   THE REACTION OF SOME PROPARGYL ALCOHOLS WITH BENZENESELENENYL CHLORIDE [J].
GARRATT, DG ;
BEAULIEU, PL ;
MORISSET, VM .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (06) :927-934