Sulfuryl chloride alkyl alcohols

The ring rearrangement of 8a-(l-hydroxy-alkyl)-hexahydro-oxazolo[3,4- ]pyridin-3-ones 163 upon treatment with sulfuryl chloride was reported in 2004 activation of the alcohol and ring extension produces 5,6-dihydro-l//-oxazolo[3,4-tf]azepin-3-ones 164 in excellent yields (Scheme 48) <2004H(63)17>. 

A related reaction is the formation of alkyl chlorosulfonates from alcohols and sulfuryl chloride. ... 

The additions of tellurium tetrahalides to olefins in the presence of alcohols proceed equally well when the tetrahalides are generated in the reaction mixture from tellurium dioxide and chlorotrimethylsilane in methanoP or concentrated hydrochloric acid/methanol. trans-2-Methoxycyclohexyl tellurium trichloride was obtained in this manner in quantitative yield . In the reactions of terminal alkenes, the TeCl3 group (from TeO and concentrated hydrochloric acid) added according to the Markovnikov rule producing 2-alkoxy-1 -alkyl tellurium trichlorides. The trichlorides were not isolated but were reduced with disodium disulfite to the ditellurium compounds, which, in turn, were converted to the tellurium trichlorides by treatment with sulfuryl chlorides. For data on these tellurium trichlorides see p. 316. The overall yields range from 15 to 70%. 

Aromatic polysulfites can be produced if bisphenols, eg, bisphenol A, are heated with diphenyl sulfite in the presence of lithium hydride (112). Halosulfates and Halosulfites. A general method for the preparation of alkyl halosulfates and halosulfites is the treatment of the alcohol with sulfuryl or thionyl chloride at low temperatures while passing an inert gas through the mixture to remove hydrogen chloride (113). 

---