1,3-DICHLOROPROPENE AS A SOURCE OF THE 1,3-DIANION DERIVED FROM PROPENE - SYNTHESIS OF UNSATURATED 1,5-DIOLS AND DIHYDROPYRANS

被引：19

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 | 1994年 / 50卷 / 46期

关键词：

D O I：

10.1016/S0040-4020(01)89335-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 1,3-dichloropropene (1, ca. 1/1 Z/E mixture) with an excess of lithium powder and a catalytic amount of 4,4'-di-tert-butylbiphenyl (DTBB, 5 mol %) in the presence of an electrophile [Me(2)CO, Et(2)CO, (CH2)(4)CO, (CH2)(5)CO, Bu(t)CHO, Me(3)SiCl] in THF at 0 degrees C affords, after hydrolysis with water, the expected unsaturated 1,5-diols 3 as a Z/E mixture or disilane (E)-4. Treatment of isolated compounds (Z)-3 with 85% phosphoric acid gives the expected dihydropyrans 5.

引用

收藏

页码：13269 / 13276

页数：8

相关论文

共 42 条

[1] N,2-DILITHIOALKYLAMINES FROM AZIRIDINES BY NAPHTHALENE-CATALYZED REDUCTIVE OPENING - SYNTHETIC APPLICATIONS [J].

ALMENA, J ;

FOUBELO, F ;

YUS, M .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3210-3215

[2] NAPHTHALENE-CATALYZED REDUCTIVE OPENING OF AZIRIDINES WITH LITHIUM - A DIRECT PREPARATION OF N-LITHIO-2-LITHIOALKYLAMINES [J].

ALMENA, J ;

FOUBELO, F ;

YUS, M .

TETRAHEDRON LETTERS, 1993, 34 (10) :1649-1652

[3] 4,4'-DI-TERT-BUTYLBIPHENYL-CATALYZED REDUCTIVE OPENING OF AZETIDINES WITH LITHIUM - A DIRECT PREPARATION OF 3,N-DILITHIOALKYLAMINES [J].

ALMENA, J ;

FOUBELO, F ;

YUS, M .

TETRAHEDRON, 1994, 50 (19) :5775-5782

[4] BETA-SUBSTITUTED ORGANO-LITHIUM COMPOUNDS FROM CHLOROHYDRINS - APPLICATION TO THE DIRECT SYNTHESIS OF BIFUNCTIONALIZED ORGANIC-COMPOUNDS [J].

BARLUENGA, J ;

FLOREZ, J ;

YUS, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (12) :3019-3026

[5]

BARRY CE, 1991, SYNLETT, P207

[6] CYCLOREVERSIONS OF ANIONS FROM TETRAHYDROFURANS - CONVENIENT SYNTHESIS OF LITHIUM ENOLATES OF ALDEHYDES [J].

BATES, RB ;

POTTER, DE ;

KROPOSKI, LM .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (04) :560-&

[7]

FUIJARRO A, 1994, TETRAHEDRON, V50, P7857

[8] NEW MASKED DELTA-LITHIOCARBONYL COMPOUNDS - PREPARATION AND SYNTHETIC APPLICATIONS [J].

GIL, JF ;

RAMON, DJ ;

YUS, M .

TETRAHEDRON, 1993, 49 (22) :4923-4938

[9] INTRAMOLECULAR 1,6-HYDRIDE TRANSFER IN ACYCLIC 1,6-DIOLS - A MECHANISTIC STUDY [J].

GIL, JF ;

RAMON, DJ ;

YUS, M .

TETRAHEDRON, 1994, 50 (24) :7307-7314

[10] REDUCTIVE OPENING OF 2-PHENYL-1,3-DIOXOLANES BY A NAPHTHALENE-CATALYZED LITHIATION - SYNTHETIC APPLICATIONS [J].

GIL, JF ;

RAMON, DJ ;

YUS, M .

TETRAHEDRON, 1993, 49 (42) :9535-9546

← 1 2 3 4 5 →