Phosphine-free conversion of alcohols into alkyl thiocyanates using trichloroisocyanuric acid/NH4SCN

被引：6

作者：

Azadi, Roya ^{[1
]}

Mokhtari, Babak ^{[1
]}

Makaremi, Mohamad-Ali ^{[1
]}

机构：

[1] Shahid Chamran Univ, Dept Chem, Coll Sci, Ahvaz 6135743337, Iran

来源：

CHINESE CHEMICAL LETTERS | 2012年 / 23卷 / 01期

关键词：

Phosphine-free; Alcohol; Thiocyanate; Trichloroisocyanuric acid; Thiocyanation; ONE-POT CONVERSION; TRIMETHYLSILYL-ETHERS; CARBOXYLIC-ACIDS; OXIDATION; REAGENT; ESTERS; THIOLS; MILD;

D O I：

10.1016/j.cclet.2011.09.022

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convenient and efficient phosphine-free procedure for the one-pot conversion of primary, secondary and tertiary alcohols into the corresponding alkyl thiocyanates or alkyl isothiocyanates is described using trichloroisocyanuric acid/NH4SCN. (C) 2011 Roya Azadi. Published by Elsevier BAT, on behalf of Chinese Chemical Society. All rights reserved.

引用

页码：77 / 80

页数：4

共 29 条

[1] TRICHLOROISOCYANURIC ACID OXIDATION OF 2-CHLORO ALDEHYDE ACETALS TO 2-CHLORO ACID-ESTERS [J].

BONI, M ;

GHELFI, F ;

PAGNONI, UM ;

PINETTI, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (01) :156-159

[2] [2,3]-SIGMATROPIC REARRANGEMENT OF AN INSITU PREPARED YLIDE AND A THIOETHER TO THIO ESTER CONVERSION AS KEY STEPS IN SHORT SYNTHESES OF SARKOMYCIN AND ITS PHENYLTHIO ESTER [J].

COHEN, T ;

KOSARYCH, Z ;

SUZUKI, K ;

YU, LC .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :2965-2968

[3] Recent developments in indole ring synthesis-methodology and applications [J].

Gribble, GW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075

[4] Preparation of alkyl nitrates, nitrites, and thiocyanates from alcohols utilizing trichloroisocyanuric acid with triphenylphosphine [J].

Hiegel, GA ;

Nguyen, J ;

Zhou, Y .

SYNTHETIC COMMUNICATIONS, 2004, 34 (14) :2507-2511

[5] Chlorine substitution reactions using trichloroisocyanuric acid with triphenylphosphine [J].

Hiegel, GA ;

Ramírez, J ;

Barr, RK .

SYNTHETIC COMMUNICATIONS, 1999, 29 (08) :1415-1419

[6] The oxidation of aldehydes to methyl esters using trichloroisocyanuric acid [J].

Hiegel, GA ;

Bayne, CD ;

Donde, Y ;

Tamashiro, GS ;

Hilberath, LA .

SYNTHETIC COMMUNICATIONS, 1996, 26 (14) :2633-2639

[7] THE OXIDATION OF SECONDARY ALCOHOLS TO KETONES WITH TRICHLOROISOCYANURIC ACID [J].

HIEGEL, GA ;

NALBANDY, M .

SYNTHETIC COMMUNICATIONS, 1992, 22 (11) :1589-1595

[8]

Iranpoor H, 1999, J CHEM RES-S, P676

[9] Conversion of alcohols, thiols, carboxylic acids, trimethylsilyl ethers, and carboxylates to thiocyanates with triphenylphosphine/diethylazodicarboxylate/NH4SCN [J].

Iranpoor, N ;

Firouzabadi, H ;

Akhlaghinia, B ;

Azadi, R .

SYNTHESIS-STUTTGART, 2004, (01) :92-96

[10] A new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highly selective bromination, thiocyanation or isothiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers [J].

Iranpoor, Nasser ;

Firouzabadi, Habib ;

Azadi, Roya .

TETRAHEDRON LETTERS, 2006, 47 (31) :5531-5534

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