Reactions of Saturated Sulphoxides and Selenoxides

Reactions of Saturated Sulphoxides and Selenoxides.—The main reactions of saturated sulphoxides and selenoxides are associated with the nucleophilic properties of the sulphinyl and seleninyl groups, and their activating effect on the adjacent saturated carbon atoms. The Pummerer rearrangement (as well as rearrangements of unsaturated sulphoxides discussed in a later section) and alkene-forming eliminations are instances of the former property the main consequence of the latter property, the formation of sulphinyl-stabilized carbanions, is covered in Chapter 2. 

An extraordinary example of a Pummerer rearrangement is that in which 

Racemization of sulphoxides in non-aqueous solvents containing HCl involves an 

Acid-catalysed exchange between sulphoxides and sulphides occurs via sulphon-ium intermediates, whereas less certainty can be asserted for the mechanistic details of the photo-metathesis PhSMe -1- PhSe(=0)Ph - PhS(=0)Me -1- PhjSe.  

MeSCH2Cl) the oxidation of cr-bromo-ketones (RCOCH2Br RCOCH2 Me2 Br- RCOCHO RCOCOSMe -h RCOCOjH -h RCOjH) the oxidation of alcohols in combination with (COCl)2, or SOCl2, or TFAA and a 

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