The Use of Sodium Dithionite for the Reduction of Imines and the Cleavage of Oximes

Abstract

Sodium dithionite reduces a variety of imines to secondary amines. Oximes are cleaved by the reagent to the parent carbonyl compound.

Synthesis and Application of a New Fluorous‐Tagged Ammonia Equivalent

“…A range of different reagents have been used for reductive cleavage of N À O bonds, which included Li/4,4'-di-tert-butylbiphenyl (DTBB), [22,23] Na/Hg amalgam, [24,25] SmI 2 , [14,[26][27][28][29][30] TiCl 3 , [31][32][33][34] indium, [8,11] LiAlH 4 , [35,36] BH 3 , [37] [Mo(CO) 6 ], [13,24,[38][39][40][41][42][43][44][45][46][47][48][49] [Co 2 (CO) 8 ], [50] [Fe(CO) 5 ], [13,51] Zn/H +, [43,[52][53][54][55] NiB 2 , [56] Na 2 S 2 O 4 , [57] [TiA C H T U N G T R E N N U N G (iPrO) 4 ]/EtMgBr, [58] NiH 2 , [59] trimethylsilyl chloride/KI, …”

Aliphatic diketones: influence of dicarbonyl spacing on amine reactivity and toxicity

“…NMR spectroscopy was performed on polylysine following incubation with 2,6-heptanedione in the presence of sodium dithionite. The NMR spectrum (Figure 3) supported 2,6-dimethylpiperidine as the structure of the reduced, covalently bound 2,6-heptanedione adduct (20,21), as predicted by the known imine-reducing ability of sodium dithionite (22) and the known cyclizing potential of -amino ketones4 {11). Integration of the peaks showed 2 2,5-Hexanedione was obtained commercially (Aldrich Chemical Co., Milwaukee, WI) and distilled prior to use, while 2,6-heptanedione and 2,7-octanedione were synthesized by established methods (15,16) with structural identity and purity confirmed by GC-MS, NMR, and mp [2,6-heptanedione, mp 30-31 °C (lit.…”

Direct Transformation of Primary Nitro Compounds into Nitriles with Sodium­ Dithionite

“…Previously, Pojer reported the reaction of oximes with aqueous sodium dithionite at room temperature that gave a similar type of carbonyl compound. 16…”