Synthesis of alkyl thiocyanates from alcohols using a polymer-supported thiocyanate ion promoted by cyanuric chloride/dimethylformamide

Abstract

A convenient procedure for one-pot conversion of alcohols into the corresponding alkyl thiocyanates in the presence of cross-linked poly (N-propyl-4-vinylpyridinium) thiocyanate ion [P4-VP]Pr-SCN, promoted by cyanuric chloride/dimethylformamide, is described. Various alcohols were converted to their corresponding alkyl thiocyanates and it was observed that substituted benzyl alcohol with electron-withdrawing or electron-donating groups were transformed into the corresponding benzyl thiocyanate derivatives in high to excellent yields in a short reaction time but, sterically hindered alcohols produced the corresponding thiocyanates in very low yields.

GRAPHICAL ABSTRACT

Keywords:

• alcohol
• benzyl thiocyanate
• polymeric reagent
• cyanuric chloride
• selectivity

Disclosure statement

No potential conflict of interest was reported by the authors.

Supplemental data

Supplemental data for this article can be accessed at doi:10.1080/17415993.2015.1035273.