Studies on the double alkylation of 2,2-disubstituted-1,3-dithiacycloalkane-S-oxides: synthesis of tertiary thiol derivatives
journal contributionposted on 07.08.2014 by Christian Fuchs, Mark Edgar, Mark Elsegood, George Weaver
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Di-alkylation of 2,2-dimethyl-1,3-dithiacycloalkane-S-oxides has been achieved allowing the synthesis of two tertiary thiol centres. The diastereoisomers of the mono-alkylated products have been shown to react at different rates. The X-ray crystal structures of three substituted dithiane-S-oxides have been determined, and the conversion of the dialkylated products into cyclic disulfide derivatives of tertiary thiols (1,2-dithiolanes) has been achieved by treatment with acid.
The authors thank Loughborough University for financial support.