Journal
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
Volume 189, Issue 6, Pages 796-802Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10426507.2013.855771
Keywords
Chlorodiphenylphosphine; alcohol; tetrahydropyranyl ether; silyl ether; thiocyanate
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Funding
- Damghan University Research Council
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A simple, highly selective and efficient method is described for the conversion of primary alcohols, tetrahydropyranyl and silyl ethers to thiocyanates by use of chlorodiphenylphosphine and ammonium thiocyanate. Secondary substrates produce both the two isomeric products, thiocyanate and isothiocyanate, while tertiary ones give isothiocyanates as the only products by this new method. In contrast to previously reported methods based on trivalent phosphorus for this transformation, the present method does not require an electrophile in the presence of trivalent phosphorus (ClPPh2). The order of activity of these substrates is silyl ether> alcohol > tetrahydropyranyl ether. The present method not only interestingly distinguishes between primary, secondary and tertiary substrates but also converts them to the corresponding thiocyanates with excellent chemoselectivity in the presence of several other functional groups.
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