Preparation of thiocyanates and isothiocyanates from alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers using triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone (DDQ)/n-Bu4NSCN system

被引：45

作者：

Iranpoor, Nasser ^{[1
]}

Firouzabadi, Habib ^{[1
]}

Nowrouzi, Najmeh ^{[1
]}

机构：

[1] Shiraz Univ, Coll Sci, Dept Chem, Shiraz 71454, Iran

来源：

TETRAHEDRON | 2006年 / 62卷 / 23期

关键词：

thiocyanation; isothiocyanation; alcohol; thiol; trimethylsilyl ether; tetrahydropyranyl ether; triphenylphosphine; DDQ;

D O I：

10.1016/j.tet.2006.03.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A combination of triphenylphosphine (PPh3) and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) provides a safe and easily available mixed reagent system for the conversion of 1 degrees and 2 degrees alcohols, thiols, trimethylsilyl-, and tetrahydropyranyl ethers to their corresponding thiocyanates and the 3 degrees ones to isothiocyanates in good to high yields. (c) 2006 Published by Elsevier Ltd.

引用

页码：5498 / 5501

页数：4

共 40 条

[1] A new and convenient method of generating alkyl isocyanates from alcohols, thiols and trimethylsilyl ethers using triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/Bu4NOCN [J].

Akhlaghinia, B .

SYNTHESIS-STUTTGART, 2005, (12) :1955-1958

[2] INORGANIC-SOLID-SUPPORTED POTASSIUM THIOCYANATE - STUDY OF REAGENT PREPARATION AND A CONVENIENT SYNTHESIS OF TERT-ALKYL THIOCYANATES [J].

ANDO, T ;

CLARK, JH ;

CORK, DG ;

FUJITA, M ;

KIMURA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04) :681-685

[3]

BOIGEGRAIN R, 1975, TETRAHEDRON LETT, V30, P2529

[4] SUGARS WITH POTENTIAL ANTIVIRAL ACTIVITY .I. CONVERSION OF HYDROXY COMPOUNDS TO NITRILES [J].

BRETT, D ;

DOWNIE, IM ;

LEE, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (03) :855-&

[5] SYNTHESIS OF ISOTHIOCYANATOPHOSPHORANES AND ISOTHIOCYANATOPHOSPHONIUM SALTS VIA OXIDATIVE ADDITION OF THIOCYANOGEN AND LIGAND SUBSTITUTION - NOVEL REAGENTS FOR CONVERTING HYDROXY-GROUPS INTO THIOCYANATE AND ISOTHIOCYANATE FUNCTIONS UNDER MILD CONDITION [J].

BURSKI, J ;

KIESZKOWSKI, J ;

MICHALSKI, J ;

PAKULSKI, M ;

SKOWRONSKA, A .

TETRAHEDRON, 1983, 39 (24) :4175-4181

[6]

BURSKI J, 1973, J CHEM SOC CHEM COMM, P940

[7]

CASTRO B, 1971, B SOC CHIM FR, P2296

[8]

CASTRO BR, 1983, ORG REACTIONS, V29, P1

[9] DIRECT ONE-STEP CONVERSION OF ALCOHOLS INTO NITRILES [J].

DAVIS, R ;

UNTCH, KG .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (14) :2985-2987

[10]

Greene T. W., 1991, PROTECTIVE GROUP ORG

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