Direct Transformation of Primary Nitro Compounds into Nitriles with Sodium­ Dithionite

Abstract

A new and practical direct transformation of primary nitro compounds into nitriles with sodium dithionite is described. The reaction is simple, convenient and eliminates the use of expensive and moisture-sensitive reagents.

Metal‐Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α‐Substituted Enantiomerically Enriched Nitriles

“…An interesting method for the synthesis of nitriles is the deoxygenation of nitroalkanes. Only few examples in the literature for this transformation exist, which involve different phosphorus compounds such as P 2 I 4 , [8] and PCl 3 , [9] sulfur compounds like Me 3 SiSSiMe 3 [8] and Na 2 S 2 O 4 , [10] or silyl derivatives such as Me 3 SiI [11] . Transformation of optically active nitroalkanes into chiral nitriles by using benzyl bromide, KOH and nBu 4 NI was reported by Carreira et al [12] …”

Simple Synthesis of Dimethyl Nitrobenzhydrylphosphonates and Heteroarylnitroarylacetonitriles via Vicarious Nucleophilic Substitution (VNS) Reaction

“…IR (film): 2954,2852,1591,1528,1494,1475,1454,1349,1254,1183,1054,1031,934,907,828,768, 700 cm -1 . 7, 156 (32), 128 (19), 127 (100), 109 (13). HRMS (EI): m/z calcd for C 13 H 14 NO 6 P: 311.0559; found: 311.0560.…”

“…IR (film): 2955IR (film): , 2852IR (film): , 1591IR (film): , 1526IR (film): , 1475IR (film): , 1351IR (film): , 1254IR (film): , 1183IR (film): , 1053IR (film): , 1033, 706 cm -1 . 8, 222 (12), 208 (19), 206 (38), 171 (40), 159 (11), 127 (9), 109 (19). HRMS (EI): m/z calcd for C 13 H 13 ClNO 5 SP 360.9941; found: 360.9935.…”

“…06,109.61,111.10,115.80,126.39,126.85,128.18,131.10,138.70,144.32,145.31. MS (EI): m/z (%) = 264 (M + + 2, 43), 262 (100), 245 (9), 227 (32), 217 (19), 216 (30), 215 (20), 204 (10), 189 (22), 188 (28), 187 (36), 181 (15), 169 15 IR (film): 3103,2927,2251,1590,1528,1473,1351,1184,11443,1119,1014,892,818, 742 cm -1 . 1 H NMR (500 MHz, CDCl 3 ):  = 5.73 (s, 1 H), 6.39-6.43 (m, 2 H), 7.42 (br s, 1 H), 7.76 (d,J = 8.6 Hz,1 H),8.20 (dd,J = 8.6,2.3 Hz, 1 H), 8.33 (d, J = 2.3 Hz, 1 H).…”

“…A series of diheteroarylacetonitriles have been obtained via reductive transformation of 1,1-diheteroaryl-2-nitroethanes. 19 On the other hand arylfuryl and arylthienylacetonitriles were not described. Some years ago we have reported that nitrodiarylacetonitriles are efficiently synthesized via VNS reaction of carbanions of -methoxy-and -phenoxyphenylacetonitriles with nitroarenes.…”