Dimethyl sulfide halogen oxides, reactions with

Dimethyl sulfoxide and chlorine form highly reactive intermediates which are of some limited use as oxidants for alcohols. These intermediates are related to those derived from the reaction of the halogens with dimethyl sulfide and probably have a structure such as (27). When formed at -4S C they allow the oxidation of primary and secondary alcdiols to aldehydes and ketones when used in a two-fold excess. For very simple alcdiols the reaction proceeds in yields of greater than 90%, but there are considerable drawbacks if some types of additional functionality are present in the molecule, e.g. alkenes react very rapidly to form vicinal dichlorides. 

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