Alkyl aryl sulphoxides synthesis

The reaction of alkyllithium reagents with diaryl or alkyl aryl sulphoxides results in a displacement of the aromatic group by the alkyl group from the alkyllithium (equation 369) . Johnson and coworkers ° were the first to apply this reaction for the synthesis of optically active alkyl methyl sulphoxides. Later on. Durst and coworkers found that the aromatic group which can best carry a negative charge is the most readily displaced, and that the lowest yields of displacement were observed when methyllithium was used as a nucleophilic reagent. The results are summarized in Table 28. 

The Andersen sulphoxide synthesis is general in scope and a large number of chiral alkyl aryl and diaryl sulphoxides became available from (—)-(S)-276 and other optically active sulphinates343-346 (Table 16). 

Arylsulphonyl radicals 879 Arylthiomethyl sulphoxides, reactions of 331 / -Arylthiovinyl sulphoxides, synthesis of 345 Aryl unsaturated alkyl sulphones, mass spectra of 137-143... 

Sultines, Sultones, and Related Systems.—A general synthesis of sultines (144) (cyclic sulphinate esters), based on the reaction of t-butyl hydroxyal-kyl sulphoxides (145) with SO2CI2 or N-chlorosuccinimide, has been developed. The method was shown to be suitable for the preparation of sultines varying in ring size from 5 to 8 and having a variety of alkyl or aryl substitution patterns. 

---