Synthesis of Organosulfur Compounds from Biomass-derived Platform Molecules

Abstract

The first part of this thesis describes efforts towards assembling a series of organosulfur compounds from a bio-based platform 5-methylthiophene-2-thiol (97). A range of S-containing functional groups such as disulfide (109), disulfide dioxide (112), disulfone (113), sulfinate ester (120), sulfide (124), sulfoxide (127), sulfone (128), dithioethane (130), thioethanol (132), thioesters (135 and 141), and β-thiocarbonyls (153, 158 and 162) were readily assembled, providing a series of organosulfur building blocks bearing several different S-functional groups. The second part of this thesis describes the development of a new route to synthesise various bio-based organosulfur compounds using elemental sulfur and cellulose-based platforms. When sulfur was used with a variety of bio-derived platform molecules under the Willgerodt-Kindler reaction conditions, over 14 different bio-based organosulfur compounds were synthesised in acceptable yields. This study has shown that valuable organosulfur compounds can be synthesised from different bio-derived molecules in the presence of elemental sulfur, a cheap and readily available chemical.