ChemInform Abstract: NITROALKYL ORGANOPHOSPHORUS COMPOUNDS. I. NITROMETHYLPHOSPHONATES

Abstract

Nitromethylphosphonate (II) können durch Nitrierung von Phosphonacetaldehyden (I) oder durch Nitrierung der β‐Äthoxyvinylphosphonate (III) hergestellt werden.

Synthesis methods of (1-aminocyclopropyl)phosphonic acids

“…The desired diazo compound was obtained from the ester of nitromethylphosphonic acid [47][48][49] {pK a 8.08 (EtOH) [50]} by the reaction of diazo transfer with trifl yl azide in the presence of pyridine; the product was purifi ed by chromatography [46] Chemagin et al [46] stated that the nitro(diethoxyphosphoryl)carbine formed under the rhodium catalysis alongside the reaction of [1+2]-cycloaddition could react as 1,3-dipole or rearrange into diethyl nitrosocarbonylphosphonate. In reaction with alkenes it led to the formation of isoxazoline N-oxides or hydroxycarbamoylphosphonates respectively; these products became predominant in the presence of electron-donor and/or bulky substituents at the double bond.…”

N-Carbamate α-aminoalkyl-p-tolylsulfones—convenient substrates in the nitro-Mannich synthesis of secondary N-carbamate protected syn-2-amino-1-nitroalkanephosphonates

“…Until now however, the reaction of diethyl nitromethanephosphonate with N-carbamate aaminoalkyl-p-tolylsulfones, as convenient precursors of unstable Ncarbamate imines, leading to the title compounds has not been described. This prompted us to present here our contribution as a new, practical synthesis of secondary 1-amino-2-nitroalkaneand 1,2-diaminoalkanephosphonates utilizing diethyl nitromethanephosphonate 13 (1) and N-carbamate a-aminoalkyl-ptolylsulfones 2 as starting materials.…”

Synthesis of glycosyl phosphonates and related compounds

“…We expected that the reaction of dialkyl phosphite anions with halonitroalkanes and 1 -nitrosulfones reported by Russell and Hershberger [7] to give 1-nitrophosphonates [8] would proceed similarly with halonitroethers, which we knew to undergo SRNl reactions with weakly basic carbanions [9]. As tert nitroethers are smoothly reduced [lo] and as halonitroethers of type 7 are easily available from the corresponding aldose oximes [4,111, the proposed sequence seemed promising.…”