The Journal of organic chemistry

Selective conversion of alcohols into alkyl iodides using a thioiminium salt

AR Ellwood, MJ Porter

Index: Ellwood, Adam R.; Porter, Michael J. Journal of Organic Chemistry, 2009 , vol. 74, # 20 p. 7982 - 7985

Full Text: HTML

Citation Number: 16

Abstract

In this note we describe a procedure for the efficient conversion of a wide range of primary and secondary alcohols to the corresponding iodides under essentially neutral conditions by treatment with the stable thioiminium salt N,N-dimethyl-N-(methylsulfanylmethylene)ammonium iodide. The byproducts of the reaction are readily removed from the desired alkyl iodides. ... The origin of this process lies in our observation that the hydrolysis of thiolactam 1 using ...