Conversion of alcohols, thiols, and trimethysilyl ethers to alkyl cyanides using triphenylphosphine/2, 3-dichloro-5, 6-dicyanobenzoquinone/n-Bu4NCN

N Iranpoor, H Firouzabadi, B Akhlaghinia…

Index: Iranpoor, Nasser; Firouzabadi, Habib; Akhlaghinia, Batool; Nowrouzi, Najmeh Journal of Organic Chemistry, 2004 , vol. 69, # 7 p. 2562 - 2564

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Citation Number: 57

Abstract

Triphenylphosphine and 2, 3-dichloro-5, 6-dicyanobenzoquinone afford an adduct, which in the presence of n-Bu4NCN converts alcohols, thiols, and trimethylsilyl ethers into their corresponding alkyl cyanides in good to excellent yields at room temperature. This method is highly selective for the conversion of 1° alcohols in the presence of 2° and 3° ones, thiols and silyl ethers.

~97%

~97%

~94%

~40%

~89%

~89%

~89%

~71%

~90%

~81%

~92%

~94%

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~90%

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~69%

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