1-(Acylamino)alkylphosphonic Acids—Alkaline Deacylation

Abstract

The alkaline deacylation of a representative series of 1-(acylamino)alkylphosphonic acids [(AC)-AAP: (AC) = Ac, TFA, Bz; AAP = GlyP, AlaP, ValP, PglP and PheP] in an aqueous solution of KOH (2M) was investigated. The results suggested a two-stage reaction mechanism with a quick interaction of the hydroxyl ion on the carbonyl function of the amide R-C(O)-N(H)- group in the first stage, which leads to instant formation of the intermediary acyl-hydroxyl adducts of R-C(O−)2-N(H)-, visible in the 31P NMR spectra. In the second stage, these intermediates decompose slowly by splitting of the RC(O−)2-N(H)- function with the subsequent formation of 1-aminoalkylphosphonate and carboxylate ions.

Deposition of Copper on Poly(Lactide) Non-Woven Fabrics by Magnetron Sputtering—Fabrication of New Multi-Functional, Antimicrobial Composite Materials

“…Air permeability of PLA samples was tested according to EN ISO 9237:1998 [ 63 ], analogously as samples of PP [ 59 ] and/or PLA [ 60 ] nonwovens. An FX 3300 Textest AG (Klimatest, Wroclaw, Poland) permeability tester was used.…”

“…As a part of our experimentation program focused on phosphonic acids [ 56 , 57 , 58 , 59 ] and textile chemistry of their hybrids with a polymer matrix [ 60 , 61 ], we present the preparation, and characterization of a new multifunctional, biodegradable composite material, PLA–Cu, composite. This composite was obtained by a surface modification of melt-blown poly(lactide) non-wovens with copper, using the direct current (DC) magnetron sputtering method.…”

Deamination of 1-Aminoalkylphosphonic Acids: Reaction Intermediates and Selectivity

“…Surprisingly, further transformations of 1-aminoalkylphosphonic acids and their reactivity as reaction substrates in organic synthesis are scarcely described in the literature [27][28][29][30][31][32][33]. Those described include among others alkaline deacylation of 1-(acylamino)alkylphosphonic acids, ref.…”

“…Those described include among others alkaline deacylation of 1-(acylamino)alkylphosphonic acids, ref. [31] oxidative dephosphorylation of 1-aminoalkylphosphonic acids [32], oxidation of 1-(N,N-dialkylamino)-alkylphosphonic acids leading to corresponding N,N-dialkyl-N-oxide derivatives [30], or recently effective preparation of 1-aminoalkylphosphonic acid quaternary ammonium salts from simple 1-aminoalkylphosphonic acid [27]. On the other hand, the use of analogous 2-aminoalkanoic acids as substrates, particularly in diazotization reaction, is a well-known methodology that yields 2-hydroxyalkanoic acids or 2-chloroalkanoic acids (Scheme 1a) [34][35][36][37], useful building blocks in medicinal chemistry [38][39][40], total synthesis of natural products [41][42][43], and polymer chemistry [44][45][46].…”

Michaelis-Arbuzov-Type Reaction of 1-Imidoalkyltriarylphosphonium Salts with Selected Phosphorus Nucleophiles

“…The chemistry of phosphorus analogs of α-amino acids has enjoyed unflagging interest for decades [1,2,3,4,5,6,7,8,9,10]. The replacement of flat carboxylic moiety with either the phosphonyl, phosphinyl, or phosphinoyl group in the structure of α-amino acids enables them to have extremely valuable biological properties.…”