A Convenient Reduction of α,β-Unsaturated Nitroalkenes to Alkylamines Using Boron Hydrides

Organometallic nitrosyl chemistry. 36. Syntheses and properties of anionic and neutral radical complexes containing CpM(NO)2 Groups (M = Cr, Mo, or W)

“…2, 1988 485 alkyl or aryl groups) each exhibit a two-electron, irreversible reduction, e.g. CpFe(CO)2Me + 2e" -[CpFe(CO)2]-+ Me" (3) or, as in the case of some of the phosphine-substituted compounds, two one-electron, irreversible reductions. In any event, reduction of these carbonyl compounds results in scission of the Fe-R bonds.…”

“…4 Only for CpCr-(NO)2X (X = halide) does this reaction yield the corresponding alkyl or aryl compounds. 3 The CpM(NO)2R (M = Mo, W; R = alkyl or aryl) compounds can be prepared from CpM(NO)2Cl (M = Mo, W) and CpM(NO)2BF4 precursors only by using relatively mild alkylating agents such as organoaluminum,4 organotin,5 or organoboron5 compounds, as appropriate. Furthermore, the CpM-(N0)2C1 (M = Mo, W) compounds decompose upon treatment with reducing metals such as Na or Zn4 while CpCr(NO)2Cl can be converted cleanly to the dimer (1) Organometallic Nitrosyl Chemistry.…”

An Evaluation of the Potential for Clandestine Manufacture of 3,4-Methylenedioxyamphetamine (MDA) Analogs and Homologs

“…A substantial amount of literature has been devoted to the synthesis and reduction of nitro alkenes [17][18][19]24,29,30,32,35,37,[62][63][64][65][66][67][68][69][70] (Scheme 8, Fig. 3, and Scheme 10, is commercially available and easily synthesized [62,63].…”

Conjugated nitroalkenes: versatile intermediates in organic synthesis

“…This was not isolated but converted directly to 45 The conversion of nitroalkenes to alkylamines has been accomplished by the use of lithium aluminum hydride, catalytic hydrogenation, or electrochemical methods.1 It has recently been reported that excess borane reduces nitroalkenes to amines at room temperature when used in THF solution in the presence of a catalytic amount of sodium borohydride. 39 A variation of the sodium borohydride catalyzed borane reduction has also been reported to yield N-substituted hydroxylamines. 40 In this method, only 1 equiv of borane to nitroalkene is used.…”