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
Full Text: HTML
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.
Related Articles:
[Radulovic, Niko S.; Dekic, Milan S.; Stojanovic-Radic, Zorica Z. Phytochemistry Letters, 2012 , vol. 5, # 2 p. 351 - 357]
[Kiasat, Ali Reza; Nazari, Simin Journal of Molecular Catalysis A: Chemical, 2012 , vol. 365, p. 80 - 86]
[Deshmukh, Swapnil S.; Huddar, Sameerana N.; Jadhav, Ravindra R.; Akamanchi, Krishnacharya G. Tetrahedron Letters, 2011 , vol. 52, # 35 p. 4533 - 4536]
A General Method for the Direct α??Arylation of Nitriles with Aryl Chlorides
[You, Jingsong; Verkade, John G. Angewandte Chemie - International Edition, 2003 , vol. 42, # 41 p. 5051 - 5053]
[Chakraborti, Asit K.; Kaur, Gurmeet Tetrahedron, 1999 , vol. 55, # 46 p. 13265 - 13268]