A preparative scale reduction of alkyl disulfides with tributyl phosphine and water

被引：23

作者：

Ayers, JT ^{[1
]}

Anderson, SR ^{[1
]}

机构：

[1] Trinity Coll, Dept Chem, Hartford, CT 06106 USA

来源：

SYNTHETIC COMMUNICATIONS | 1999年 / 29卷 / 03期

关键词：

D O I：

10.1080/00397919908085777

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of alkyl disulfides has been shown to be reduced by tributyl phosphine at room temperature. The resulting thiols were then acylated in the same pot and isolated in good yields. This sequence is convenient and is a practical option for the preparation of gram quantities of thiol or thioester from the corresponding disulfide.

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页码：351 / 358

页数：8

相关论文

共 20 条

[1] REDUCTIVE CLEAVAGE OF AROMATIC DISULFIDES USING A POLYMER-SUPPORTED PHOSPHINE REAGENT [J].

AMOS, RA ;

FAWCETT, SM .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (14) :2637-2639

[2] CHROMATOGRAPHIC METHOD FOR THE QUANTITATIVE-ANALYSIS OF THE DEPROTECTION OF DITHIASUCCINOYL (DTS) AMINO-ACIDS [J].

BARANY, G ;

MERRIFIELD, RB .

ANALYTICAL BIOCHEMISTRY, 1979, 95 (01) :160-170

[3] SELECTIVE REDUCTIONS .33. POTASSIUM TRIISOPROPOXYBOROHYDRIDE AS A SELECTIVE REDUCING AGENT IN ORGANIC-SYNTHESIS - REACTION WITH SELECTED ORGANIC-COMPOUNDS CONTAINING REPRESENTATIVE FUNCTIONAL-GROUPS [J].

BROWN, HC ;

CHA, JS ;

NAZER, B ;

KIM, SC ;

KRISHNAMURTHY, S ;

BROWN, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (05) :885-892

[4] SELECTIVE REDUCTIONS .9. REACTION OF LITHIUM ALUMINUM HYDRIDE WITH SELECTED ORGANIC COMPOUNDS CONTAINING REPRESENTATIVE FUNCTIONAL GROUPS [J].

BROWN, HC ;

WEISSMAN, PM ;

YOON, NM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (07) :1458-&

[5]

BROWN HC, 1984, SYNTHESIS-STUTTGART, P498

[6]

CHA JS, 1992, B KOR CHEM SOC, V13, P702

[7] OXIDATION OF TRIVALENT PHOSPHORUS COMPOUNDS BY DISULPHIDES [J].

DAVIDSON, RS .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (21) :2131-&

[8] STUDIES IN ORGANIC SULFUR COMPOUNDS .9. PREPARATION AND DESULFURIZATION OF OPTICALLY ACTIVE 1,1-DIPHENYL-3-MERCAPTOPROPAN-2-OL [J].

DJERASSI, C ;

GROSSMAN, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (10) :2553-2555

[9] CONVENIENT AND STEREOSELECTIVE DITHIOL SYNTHESIS [J].

ELIEL, EL ;

RAO, VS ;

SMITH, S ;

HUTCHINS, RO .

JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (04) :524-526

[10] BIOSYNTHESIS AND STRUCTURE OF LIPOIC ACID DERIVATIVES [J].

GUNSALUS, IC ;

BARTON, LS ;

GRUBER, W .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (08) :1763-1766