Mechanism of sodium dithionite in solubility tedt
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Dithionite reduction
Sodium dithionite reduction of pyridinium salts, usually substituted with electron-withdrawing groups in the 3- or 3,5-positions, chiefly affords the corresponding 1,4-dihydropyridines. The regioselectivity of formation of the dithionite adducts and mechanisms of decomposition have been studied <2005T10331, 2000TL1235>. The sodium dithionite reduction of pyridinium salts 172 and 174 gave the 1,4-dihydropyridines 173 and 175, respectively (Equations 91 and 92) <1997JOC729, 2002T7869>.
(91)
(92)
Lavilla and co-workers developed a dithionite reduction of α-substituted N-alkylpyridinium salts to afford the corresponding 1,4-dihydropyridines or piperidines. In the absence of NaHCO3, full reduction occurred to give the piperidine derivatives in high yield (Scheme 32) <2005TL3513>.
Sodium dithionite reduction of pyridinium salts, usually substituted with electron-withdrawing groups in the 3- or 3,5-positions, chiefly affords the corresponding 1,4-dihydropyridines. The regioselectivity of formation of the dithionite adducts and mechanisms of decomposition have been studied <2005T10331, 2000TL1235>. The sodium dithionite reduction of pyridinium salts 172 and 174 gave the 1,4-dihydropyridines 173 and 175, respectively (Equations 91 and 92) <1997JOC729, 2002T7869>.
(91)
(92)
Lavilla and co-workers developed a dithionite reduction of α-substituted N-alkylpyridinium salts to afford the corresponding 1,4-dihydropyridines or piperidines. In the absence of NaHCO3, full reduction occurred to give the piperidine derivatives in high yield (Scheme 32) <2005TL3513>.
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