THE HYDROBORATION OF 1-ALKYLTHIO-1-ALKYNES, AND ITS APPLICATION TO THE SYNTHESES OF S-ALKYL ALKANETHIOATES AND (Z)-1-ALKYLTHIO-1-ALKENES

被引：22

作者：

HOSHI, M ^{[1
]}

MASUDA, Y ^{[1
]}

ARASE, A ^{[1
]}

机构：

[1] KITAMI INST TECHNOL, DEPT IND CHEM, KITAMI, HOKKAIDO 090, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1990年 / 63卷 / 02期

关键词：

D O I：

10.1246/bcsj.63.447

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hydroboration of 1-alkylthio-1-alkynes with dicyclohexylborane or bis(1,2-dimethylpropyl)borane proceeded smoothly, adding most of the dialkylboryl group to the α-position of the triple bond. The resulting alkenylboranes afforded either S-alkyl alkanethioates on a controlled oxidation with alkaline hydrogen peroxide in the presence of N,N,N',N'-tetramethylethylenediamine or (Z)-1-alkylthio-1-alkenes on a basic protonolysis, successive treatments with methyllithium, copper(I) iodide and water in the presence of hexamethylphosphoric triamide.

引用

页码：447 / 452

页数：6

共 17 条

[1]

ALEXAKIS A, 1985, SYNTHESIS-STUTTGART, P72

[2]

Baker R. B., 1929, J AM CHEM SOC, V51, P1567

[3]

BARRETT GC, 1979, COMPREHENSIVE ORG 11, V3

[4]

BROWN HC, 1980, ORGANIC SYNTHESIS TO, P121

[5]

HARPP DN, 1979, SYNTHESIS-STUTTGART, P181

[6] SYNTHESIS OF S-ALKYL ALKANETHIOATES VIA 1-LODOALK-1-ENYLDIALKYLBORANES [J].

HOSHI, M ;

MASUDA, Y ;

ARASE, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (11) :714-715

[7] STEREOSPECIFIC SYNTHESIS OF (E)-VINYL SULFIDES VIA 1-IODOALK-1-ENYLDIALKYLBORANES [J].

HOSHI, M ;

MASUDA, Y ;

ARASE, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1068-1069

[8]

MATTESON DS, 1987, CHEM METAL CARBON BO, V4, pCH3

[9] NOVEL INTERMOLECULAR TRANSFER-REACTION OF ALKENYLTRIALKYLBORATES WITH AQUEOUS BASES AND ITS APPLICATION TO PROTONOLYSIS OF ALKENYLBORON DERIVATIVES [J].

NEGISHI, E ;

CHIU, KW .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (21) :3484-3486

[10] HIGHLY STEREOSELECTIVE AND GENERAL SYNTHESIS OF CONJUGATED TRANS,TRANS-DIENES AND TRANS-ALKYL KETONES VIA HYDROBORATION [J].

NEGISHI, E ;

YOSHIDA, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (17) :606-607

← 1 2 →