Conversion of alcohols, thiols, carboxylic acids, trimethylsilyl ethers, and carboxylates to thiocyanates with triphenylphosphine/diethylazodicarboxylate/NH4SCN

N Iranpoor, H Firouzabadi, B Akhlaghinia, R Azadi

Index: Iranpoor, Nasser; Firouzabadi, Habib; Akhlaghinia, Batool; Azadi, Roya Synthesis, 2004 , # 1 p. 92 - 96

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Citation Number: 33

Abstract

In continuation of our studies for the preparation of thiocyanates [13-15] we wish to report on the use of PPh 3 /DEAD/NH 4 SCN for the efficient conversion of alcohols, thiols, carboxylic acids, silyl ethers and silyl carboxylates to their corresponding thiocyanates. In this method which is a development of the Mitsunobu reaction, [16] [17] the use of NH 4 SCN as source of thiocyanate ion instead of (SCN) 2 provides a safe, simple, and highly chemoselective method for the ...