Linear Oligosulfoxides: Synthesis and Solubility Studies.

ABSTRACT: Synthesis of three linear oligosulfoxides containing up to six sulfoxide groups was achieved by multiple SN2 reactions between an alkanethiol and alkyl tosylate to give a linear oligosulfide followed by oxidation of the oligosulfide with sodium periodate to give an oligosulfoxide. The challenge of complete avoidance of partial oxidation and over oxidation was easily overcome using the sodium periodate oxidation conditions. Although sulfoxide is a highly polar functional group, the oligosulfoxides were found to have limited solubility in many solvents including DMSO and water, which disobeys the "like dissolves like" rule. The surprising solubility pattern of oligosulfoxides was discussed in the context of the drastically different solubility patterns of polyethylene glycol (PEG), poly(buty

SUBMITTER: Halami B 

PROVIDER: S-EPMC6884079 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature