DTBB-CATALYZED LITHIATION OF 1,4-DICHLORO-2-BUTYNE UNDER BARBIER CONDITIONS - SYNTHESIS OF FUNCTIONALIZED ALKYNES

被引：20

作者：

GUIJARRO, A ^{[1
]}

YUS, M ^{[1
]}

机构：

[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALACANT,SPAIN

来源：

TETRAHEDRON | 1995年 / 51卷 / 01期

关键词：

D O I：

10.1016/0040-4020(94)00936-O

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 1,2-dichloro-2-butyne (1) with an excess of lithium powder and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB, 2.5 mol %) in the presence of an electrophile [Me(3)SiCl, Bu(t)CHO, Me(2)CO, Et(2)CO, (CH2)(4)CO, (CH2)(5)CO, (CH2)(7)CO] in THF at -40 degrees C leads, after hydrolysis with water, to the corresponding disubstituted acetylenes 2 in moderate yields.

引用

页码：231 / 234

页数：4

共 16 条

[1] BUBNOV YN, 1989, METALLOORGAN KHIMIYA, V2, P1433
[2] NAPHTHALENE-CATALYZED LITHIATION OF 3-CHLORO-2-CHLOROMETHYLPROPENE IN A BARBIER-TYPE PROCESS WITH CARBONYL-COMPOUNDS
GOMEZ, C
RAMON, DJ
YUS, M
[J]. TETRAHEDRON, 1993, 49 (19) : 4117 - 4126
[3] ARENE-CATALYZED LITHIATION OF 1,4-DICHLOROBUT-2-ENES AND 3,4-DICHLOROBUT-1-ENE AND REACTION WITH ELECTROPHILES - A COMMON REACTION PATHWAY
GUIJARRO, A
YUS, M
[J]. TETRAHEDRON, 1994, 50 (26) : 7857 - 7864
[4] DICHLOROMETHANE AS A SOURCE OF THE CH22-SYNTHON - A COMBINATION OF AN ARENE-CATALYZED LITHIATION AND A BARBIER-TYPE REACTION
GUIJARRO, A
YUS, M
[J]. TETRAHEDRON LETTERS, 1994, 35 (02) : 253 - 256
[5] 4,4'-DI-TERT-BUTYLBIPHENYL-CATALYZED LITHIATION OF 2,3-DICHLOROPROPENE - A BARBIER-TYPE PRACTICAL ALTERNATIVE TO 2,3-DILITHIOPROPENE
GUIJARRO, A
YUS, M
[J]. TETRAHEDRON LETTERS, 1993, 34 (12) : 2011 - 2014
[6] GUIJARRO A, UNPUB TETRAHEDRON
[7] METALATION REACTIONS .14. GENERALITY OF 1,3-SIGMATROPIC SHIFT OF HYDROGEN IN ALLENYLLITHIUM COMPOUNDS
KLEIN, J
BECKER, JY
[J]. TETRAHEDRON, 1972, 28 (21) : 5385 - &
[8] LEBEDEVA AI, 1951, ZH OBSHCH KHIM, V21, P1825
[9] Maercker A, 1987, TOP CURR CHEM, V138, P1
[10] PRONOUNCED CONFORMATIONAL PREFERENCES IN 1,4-DISUBSTITUTED BUT-2-YNES
RADOM, L
STILES, PJ
VINCENT, MA
[J]. JOURNAL OF MOLECULAR STRUCTURE, 1978, 48 (02) : 259 - 270

← 1 2 →