K 2 S 2 O 8 -mediated nitration of alkenes with NaNO 2 and 2,2,6,6-tetramethylpiperidine-1-oxyl: stereoselective synthesis of ( E )-nitroalkenes

Ionic‐Liquid Controlled Nitration of Double Bond: Highly Selective Synthesis of Nitrostyrenes and Benzonitriles

“…As already reported, this can be due to I – anion that can promote C‐H substitution through a I + species intermediate. [16b] However, the reaction in TBAI was complicated by the formation of molecular iodine, by means of a redox reaction involving NO 2 – anion which destroyed the IL medium (2I – + NO 2 – + 2H + → I 2 + NO + H 2 O). Therefore, TBAI was excluded from any other investigation.…”

“…Recently, sodium nitrite has been found to function as a green and cheap nitrogen source used to give the simple C–H nitration or the C–C bond cleavage,, [9a] avoiding the use of highly toxic cyanides and expensive metals. However, also these methods require the assistance of oxidants, radical catalysts, Lewis or Brønsted acids, toxic solvents, or other additives (Figure ).…”

Metal-free, room temperature, acid-K2S2O8 mediated method for the nitration of olefins: an easy approach for the synthesis of nitroolefins

“…1, right side, upper half). [11][12][13][14] In the similar pattern, Guo et al also developed another method using combination of sodium nitrite (NaNO 2 ), potassium persulfate and TEMPO ( Fig. 1, right side, upper half).…”

“…1, right side, upper half). 14 In another attempt, Kuhakarn et al reported the stereo-selective nitration of olen using radical based species generating from the reaction of sodium nitrite (NaNO 2 ), oxone and potassium iodide ( Fig. 1, lower half).…”

Applications of Sodium Nitrite in Organic Synthesis

“…In an alternative approach, Guo et al reported stereoselective nitration of alkenes 38 with NaNO 2 in the presence of K 2 S 2 O 8 and TEMPO (Scheme ) . The study to assess the scope inferred that whereas mono substituted and disubstituted alkenes with R 1 = R 2 afforded ( E ) stereoisomer only, multi substituted alkenes bearing R 1 ≠ R 2 gave a mixture of ( E ) and ( Z ) stereoisomers with ( E ) isomer as the major product.…”