Preparation and Reactions of Some Cyclic Orthoester Derivatives

Article abstract of DOI:10.1016/S0040-4020(01)81741-5

Deprotonation of the alkoxysulphone (5) followed by quenching with diphenyl disulphide yields the dithioorthoester (6) and not the expected ketene monothioacetal (7).Attempts at orthoester exchange of (6) with decanol with a variety of reagents lead to ring opened products.Quenching of the anion derived from (5) with sulphuryl chloride or bromine leads respectively to the chloride (19) and bromide (20).Solvolysis of these halides leads to formation of sulphinate esters.