Cyclic 1,3-diol monosulfonate

Fragmentation-type ring opening of cyclic diol monosulfonates... [Pg.520]

The great utility of fragmentations, especially those of 1,3-diol monosulfonates, for the construction of functionalized, medium-sized cycloalkenes was developed by Wharton, by applying previous results. In recognition of his important contributions to the chemistry of heterolytic fragmentations of cyclic 1,3-diol derivatives, this reaction type has been referred to in a recent review as the Wharton fragmentation . ... [Pg.1042]

Wharton fragmentation Base-induced formation of medium-sized cyclic alkenes from 1,3-diol monosulfonates. 480... [Pg.509]

Monosulfonation of primary and secondary diols can generally be accomplished under controlled conditions. The selective tosylation of diol (54), followed by reaction with trimethylamine in a sealed tube and ion exchange with Dowex-1 (Cl") resin gave (+)-muscarine chloride (55 Scheme 23). ° Intramolecular alkylation of cyclic amine (56) gave quaternary ammonium salt (57) subsequent hydrogenolysis of the benzyl group in (57) afforded (58 Scheme 23). ... [Pg.74]

Big Chemical Encyclopedia