Facile Ring-Expansion Substitution Reactions of 1,3-Dithiolanes and 1,3-Dithianes Initiated by Electrophilic Reagents to Produce Monohalo-,-cyano-, -azido- and -thiocyanato-1,4-dithiins and -1,4-dithiepins

Mild and convenient methods for the high yielding ring-expansion substitution reactions of 1,3-dithiolanes and 1,3-dithianes generated from different aryl methyl ketones using different electrophilic reagents are reported. In this study, facile preparations of monohalo-, -cyano-, -azido-, -thiocy- anato-1,4-dithiins and -1,4-dithiepins are described. A general mechanism is also proposed for the reactions described in this article

Ring-expansion / Electrophilic substitution / 1,3-Dithiolane / 1,3-Dithiane / 1,4-Dithiin / 1,4-Dithiepin / N-Halosuccinimide / N-Thiocyanatosuccinimide / N-Cyanosuccinimide / N-Azidosuccinimide