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Disulfones, from dithioacetal oxidation

A novel method for the synthesis of alkenes is based on the coupling of aldehydes with dithioacetals to give the corresponding hydroxy thioacetals, which afford vicinal disulfides via reductive phenylthio migration.242 The syn-diastereomers are the major products from symmetrical compounds while the anti-isomers are obtained with high selectivity with unsymmetrical compounds. Separation of the diastereomers, oxidation to the 1,2-disulfones, and reductive elimination give the corresponding alkenes with moderate stereoselectivities (Eq. 137).242... [Pg.414]

Finally MacDonald and Fischer have prepared the free ajyZo-pento-dialdose (8) by the sulfone-degradation method. The diethyl dithioacetal of scyllo-inosose (12) was oxidized to the corresponding disulfone which, on treatment with ammonia, gave the dialdose (8). The structure was proved by converting the compound into the bis(ethylene dithioacetal) derivative, which was identical with that obtained from a /io-pentodialdose prepared by a previous method. ... [Pg.232]

See other pages where Disulfones, from dithioacetal oxidation is mentioned: [Pg.324]    [Pg.179]    [Pg.195]    [Pg.82]    [Pg.86]    [Pg.133]    [Pg.145]   
See also in sourсe #XX -- [ Pg.32 , Pg.82 , Pg.83 , Pg.84 , Pg.85 , Pg.86 , Pg.87 ]

See also in sourсe #XX -- [ Pg.82 , Pg.83 , Pg.84 , Pg.85 , Pg.86 , Pg.87 ]



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