Showing papers in "Phosphorus Sulfur and Silicon and The Related Elements in 1991"
TL;DR: Aminophosphonates are analogues of amino acids in which a carboxylic moiety is replaced by phosphonic acid or related groups that inhibit enzymes involved in amino acid metabolism and thus affect the physiological activity of the cell.
Abstract: Aminophosphonates are analogues of amino acids in which a carboxylic moiety is replaced by phosphonic acid or related groups. Acting as antagonists of amino acids, they inhibit enzymes involved in amino acid metabolism and thus affect the physiological activity of the cell. These effects may be exerted as antibacterial, plant growth regulatory or neuromodulatory. Chosen representative examples of biologically active aminophosphonates are presented in some detail.
899 citations
TL;DR: In this paper, an improved method of synthesizing thiosemicarbones is proposed, which should be efficient, high yield, general, and safe (avoids toxic or unpleasant reagents).
Abstract: Thiosemicarbazones of α-(N)-heterocyclic ketones and aldehydes possess a broad spectrum of potentially useful chemotherapeutic activities. Thus, the antimalarial, antibacterial, and antiviral properties of this class have been explored by Klayman, et al.1 The antileishmanial activity of a series of acetyl β-carboline thiosemicarbazones was recently described by Dodd and coworkers .2 The α-(N)-heterocyclic thiosemicarbazones act as tridentate ligands for transition metals3; this property has been implicated in their biological mechanism of action.4 The synthesis thiosemicarbazone-transition metal complexes and the spectroscopic investigation of structure and bonding in these complexes is being actively pursued 5 In order to facilitate these investigations, an improved method of synthesizing thiosemicarbones is desirable. Such a synthesis should be efficient (high yield), general (afford thiosemicarbazones of N4-monosubstitution or N4,N4-disubstitution patterns), safe (avoids toxic or unpleasant re...
144 citations
TL;DR: In this article, physical and spectroscopic properties of amino-arylmethylphosphonic-and -phosphonous acids, the phosphorus analogues of phenylglycine, are described.
Abstract: The preparation, physical and spectroscopic properties of amino-arylmethylphosphonic- and -phosphonous acids, the phosphorus analogues of phenylglycine, are described. It is shown that several of the compounds prepared exhibit antifungal activity at 200 ppm. Thus 1e, 1f, 1g and 1h showed activity against Erysiphe (barley), 2a against Puccinia (wheat) and 6a against Botrytis (apple). Of particular interest is the high gameticidal activity of 3a in the greenhouse.
118 citations
TL;DR: In this article, the synthesis of 1-amino-2-(4-fluorophenyl)ethylphosphonic acid with dibenzoyltartrate is described.
Abstract: Resolution of racemic 1-amino-2-(4-fluorophenyl)ethylphosphonic acid with dibenzoyltartrate is easily accomplished. In the inhibition of PAL 2b(-) is about five times as active as 2a(+). The synthesis of the dipeptides 5a and 5b, and of the tripeptides 8a and 8b is described and comments are made on their biological activity.
94 citations
TL;DR: In this article, 1-Amino-2-(o, m, and p-pyridyl)-ethylphosphonic acids, 5α, 5β and 5γ, have been prepared by alkylation of benzylideneaminomethylphosphonate, followed by hydrogenation and hydrolysis.
Abstract: 1-Amino-2-(o, m, and p-pyridyl)-ethylphosphonic acids, 5α, 5β and 5γ, have been prepared by alkylation of benzylideneaminomethylphosphonate, followed by hydrogenation and hydrolysis, whereas 1-amino- 2-(o, m, and p-methoxyphenyl)-ethyl phosphonic acids, 5i, 5k, and 51 and some other derivatives were obtained from the oximes by hydrogenation and hydrolysis. 1-Amino-2-pyridylethylphosphonic acids, 5α, 5β, and 5γ, and 1-amino-2-(alkoxy-substituted phenyl)- ethylphosphonic acids, 51, 5m, and 5n and others such as 5u show activity against Botrytis cinerea (on apple) and Cercospora (on peanuts). 5q is an inhibitor of anthocyanin synthesis in vivo. 3t exhibits activity against Piricularia (on rice) and 3w is active against Phytophthora (on tomato) and Plasmopora (on grapes).
38 citations
TL;DR: In this article, the synthesis and properties of a key intermediate for arsonolipids, rac-1,2-dihydroxypropyl-3-arsonic acid and its salts, are described.
Abstract: The synthesis and properties of a key intermediate for arsonolipids, rac-1,2-dihydroxypropyl-3-arsonic acid and its salts, are described. The mechanism of the Meyer reaction with β-hydroxy alkyl halides is discussed.
37 citations
TL;DR: In this article, a new class of lipids, arsonolipids or rac-1,2-diacyloxypropyl-3-arsonic acids, have been synthesized by acylating tetrabutyl ammonium hydrogen with myristic, palmitic and stearic anhydrides in the presence of pyridine.
Abstract: A new class of lipids, arsonolipids or rac-1,2-diacyloxypropyl-3-arsonic acids, have been synthesized by acylating tetrabutyl ammonium hydrogen rac-1,2-dihydroxypropyl-3-arsonate with myristic, palmitic and stearic anhydrides in the presence of pyridine. The yields are moderate to low due to decomposition of rac-1,2-dihydroxypropyl-3-arsonic acid and its salts by acylating agents. Acid salts of arsonolipids were prepared by neutralization but neutral salts could not be made.
35 citations
TL;DR: In this paper, the influence of catalyst and solvent on the conformational requirements of the complex formed was discussed on the basis of the conformations of the resulting complex. But the influence on the resulting conformations was not investigated.
Abstract: For the evaluation of the predominating factors controlling the stereochemical process of the addition of dialkylphosphite to a chiral Schiffs base resulting from condensation of substituted benzaldehyde and 1-phenylethylamine, various structural effect of the substrates and phosphorus reagents were investigated. The influence of catalyst and solvent is discussed on the basis of the conformational requirements of the complex formed.
32 citations
TL;DR: Alkylation of 2-mercapto-3-cyano-4-aryl-5,6,7,8-tetrahydroquinoline (I) gave compounds II-IV as mentioned in this paper.
Abstract: Alkylation of 2-mercapto-3-cyano-4-aryl-5,6,7,8-tetrahydroquinoline (I) gave compounds II–IV. Cyclization of III and IV afforded thienoquinolines V and VI respectively. On diazotization of V and VI, the corresponding triazinone derivatives VII and VIII were obtained. Also, reaction of V with benzoyl chloride yielded the tetracyclic compound IX. Structures of the new compounds were established by their elemental analyses and spectral data. Some of these compounds were screened in vitro for their antibacterial activities.
31 citations
TL;DR: In this paper, the synthesis of 3-chloropentan-2.4-dione was used as starting material to synthesize other heterocyclic compounds, such as pyrazolo and isoxazole.
Abstract: 2-Acetyl-6-cyano-7-ethyl-3-methylthiazolo[3.2-a]-pyrimidine-S-one (3) prepared by reaction of compound (1) with 3-chloropentan-2.4-dione followed by ring closure, was used as starting material to synthesise other heterocyclic compounds. The acetyl compound (3) was easily condensed with different amines to produce the imines (4–8). or the corresponding chalcone (9) when allowed to react with an aromatic aldehyde in presence of zinc chloride. Coupling of compound (3) with benzene diazonium chloride gave the phenylazo derivative (10). When compound (4) was treated with a-haloketones or a-haloesters, the thiazoline or thiazolidine compounds (11–15) were produced. Compound (15) was condensed with aromatic aldehydes to give the corresponding arylidene-derivatives (16a–c). Finally the chalcone (9) was reacted with hydrazine hydrate, phenyl hydrazine and hydroxyl amine to give pyrazolo and isoxazole compounds (17–19) respectively.
31 citations
TL;DR: In this article, the choice of the solvent can be crucial, especially with aromatic disulfides for which sulfur trifluoromethylation competes with nucleus one.
Abstract: Trifluoromethyl thioethers can be obtained from disulfides, sodium trifluoromethanesulfinate and an oxidizer like t-BuOOH, CAN or K2S2O8. The reaction seems to be a radical one and one half of the disulfide molecule only is used for trifluoromethylation. Yields are related to the nucleophilicity of the sulfur atoms. The choice of the solvent can be crucial, especially with aromatic disulfides for which sulfur trifluoromethylation competes with nucleus one.
TL;DR: The analysis of the carbonyl frequency shifts hyperconjugative parameters (ΔV H) along with the non-additivity effect of α-methylene carbon chemical shifts for the ethylthio- (1), ethylsulfinyl-(2) and ethyl sulfonyl- (3) propanones indicated the occurrence of both π∗ CO/σ C-SOn and πCO/σ∗C -SOn interaction in the ground state of their gauche conformers as discussed by the authors.
Abstract: The analysis of the carbonyl frequency shifts hyperconjugative parameters (ΔV H) along with the Non-Additivity Effect of the α-methylene carbon chemical shifts for the ethylthio- (1), ethylsulfinyl-(2) and ethylsulfonyl- (3) propanones indicated the occurrence of both π∗ CO/σ C-SOn and πCO/σ∗C -SOn interaction in the ground state of their gauche conformers. The bathochromicaly shifted n → π∗CO transition of the title compounds in relation to the parent compound indicated the existence of the π∗CO/σ∗C-SOn interaction in the excited state of their gauche rotamers.
TL;DR: In this article, the thermal stability of enethiolizable thioketones and dithioesters with peroxycarboxylic acid was studied and a novel rearrangement was observed.
Abstract: Direct oxidation of enethiolizable thioketones and dithioesters with a peroxycarboxylic acid affords the corresponding sulfines quantitatively. This observation stands in contrast with literature expectations, stating that this reaction would lead to divin disulfides. The oxidation shows a high stereoselectivity: delivery of the oxygen proceeds from the side opposite to the alkylthio group of dithioesters and from the side opposite to the more hindered substituent in the case of thioketones. The thermal stability of these sulfines was studied and a novel rearrangement was observed. The second part of this report deals with the thio-Claisen rearrangement of precursors bearing a chiral centre adjacent to the pericyclic nucleus and its use for stereocontrol in the acyclic series. This thermally facile transposition leads to allylated dithioesters with good to excellent yields. A high diastereomeric selectivity was obtained in a number of cases involving either a steric effect with alkyl groups on th...
TL;DR: In this article, the reaction of pyridine-2.5-Cyano-4-oxo-6-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine (P2S5) with P2S4 to give pyrimidine 2,4,dithione (II) gave the corresponding hydrazone derivatives.
Abstract: 5-Cyano-4-oxo-6-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine (I) reacts with P2S5 in pyridine to give pyrimidine-2,4-dithione (II). Further reaction of II with ethyl chloroacetate, chloroacetanilide, phenacyl bromide, bromoacetone and chloroacetonitrile gave the corresponding thieno[2,3-d]pyrimidine derivatives (III-VI). Interaction of compound IVa with hydrazine hydrate in ethanol or diluted ethanol gave the hydrazide and hydrazino derivatives (VII, IX), which reacted with aromatic aldehydes to give the corresponding hydrazones (VIIIa-c, Xa-c ). Alkaline hydrolysis of IV, using KOH gave the acid XI with extrusion of thioglycolic acid.
TL;DR: The reaction of benzenephosphonic acid (I) and SO3 in the absence of solvent, at 2.2 ≤ SO3:I mole ratio ≤ 12.7 and at 170 ≤ T(°C) ≤ 240, yields benzene-phosphono-3-sulphonic acid as discussed by the authors.
Abstract: The reaction of benzenephosphonic acid (I) and SO3 in the absence of solvent, at 2.2 ≤ SO3:I mole ratio ≤ 12.7 and at 170 ≤ T(°C) ≤ 240, yields benzenephosphono-3-sulphonic acid (II) and benzene-phosphono-3.5-disulphonic acid (III): I→SO3 II →SO3 III. In the reaction performed at atmospheric pressure (SO3:I ≃ 2.4), substantial dephosphonation occurs. Under autogenous pressure (5.2 ≤ SO3:I ≤ 12.7). complete conversion of I to III and no dephosphonation are observed.
TL;DR: A review of the literature on chlorosulfonic acid for sulfonation of aromatic compounds can be found in this article, with a focus on the use of CISO3H, a reagent that replaces one or more hydrogen atoms by the SO2CI group.
Abstract: The early work on sulfonation, chlorosulfonation and the formation of sulfonyl derivatives was reviewed by Suter1 and by Suter and Weston for aromatic hydrocarbons.2 More recent reviews of sulfonation were carried out by Gilbert3 4 Hogg5 Cerfontain6 Anderson7 and Barrett.8 In this review of the literature since 1950, we will concentrate upon the use of chlorosulfonic acid, (chlorosulfuric acid, CISO3H), to achieve the chlorosulfonation of aromatic compounds, i.e., the replacement of one or more hydrogen atoms by the chlorosulfonyl (SO2CI) group. General properties of chlorosulfonic acid and specific synthesis of a variety of sulfonic acids employing this reagent have been described.9 10
TL;DR: In this paper, the interaction of 4-phenoxy and 4-pyridyloxy substituted 1.2-dinitrobenzenes and aminoalkylphosphonates,phosphinates, and -phosphine oxides produces mainly 5-pheniox- and 5-pyrusoxy substituted 2-nitrophenylaminoalkyIphosphonsates.
Abstract: Interaction of 4-phenoxy and 4-pyridyloxy substituted 1.2-dinitrobenzenes and aminoalkylphosphonates,-phosphinates, and -phosphine oxides produces mainly 5-phenoxy- and 5-pyridyloxy substituted 2-nitrophenylaminoalkyIphosphonates. -phosphinates and -phosphine oxides (Table I to IV and Figure 1 to 5). some of which show high herbicidal and plant growth regulating activity. The herbicidal activity increases from pyridyloxy-phenylaminoalkylphosphonates to phenoxy-phenylaminoalkyl-phosphonates, -phosphinates, -phosphine oxides. Of all the compounds tested the phosphine oxide 4a was at all concentrations the most active compound.
TL;DR: In this paper, the interaction of 1,2-aIkadienephosphonic derivatives with phosphorus containing pseudohalogenes affords 2,5-dihydro-1,2oxaphospholene derivatives.
Abstract: The interaction of 1,2-aIkadienephosphonic derivatives with phosphorus containing pseudohalogenes affords 2,5-dihydro-1,2-oxaphospholene derivatives. The structure of the new compounds is determined by NMR and IR spectroscopy.
TL;DR: A series of direct reactions of red phosphorus (or white) with organyl halides, alkenes and acetylenes have been developed as discussed by the authors, and these reactions occur in superbasic systems such as alkali metal hydroxide-dipolar aprotic complexing solvent (DMSO, HMPA) or under phase-transfer conditions to afford earlier inaccessible triorganylphosphines and -phosphine oxides including unsaturated ones in good yields.
Abstract: A series of new direct reactions of red phosphorus (or white) with organyl halides, alkenes and acetylenes have been developed. Reactions occur in superbasic systems, such as alkali metal hydroxide-dipolar aprotic complexing solvent (DMSO, HMPA) or under phase-transfer conditions to afford earlier inaccessible triorganylphosphines and -phosphine oxides including unsaturated ones in good yields.
TL;DR: A new family of phosphorus heterocycles, namely 8-substituted 16H-dinaphtho[2, 1-d: 1′, 2′-g]1, 3, 2-dioxaphosphocin 8-oxides, has been obtained via a synthesis from reaction of bis(2-hydroxy-1-naphthyl)methane with a series of aryl phosphorodichloridates in dry benzene in the presence of triethylamine as discussed by the authors.
Abstract: A new family of phosphorus heterocycles, namely 8-substituted-16H-dinaphtho[2, 1-d: 1′,2′-g]1, 3, 2- dioxaphosphocin 8-oxides, has been obtained via a synthesis from reaction of bis(2-hydroxy-1-naphthyl)methane with a series of aryl phosphorodichloridates in dry benzene in the presence of triethylamine. NMR analysis of a solution of the title compounds revealed essentially no coupling between the bridged methylene protons and the P atom which suggested the dioxaphosphocin ring may exist in a boat conformation in solution. An X-ray diffraction analysis of a crystal of 8-(2′,3′-dimethylphenoxy)- 16H-dinaphtho[2,1-d:1′,2′-g]1,3,2-dioxaphosphocin 8-oxide does indicate that in the solid state the dioxaphosphocin ring is in a distorted and extended boat-like conformation with the P[dbnd]O and bridged CH2 groups directed away from each other. Electron impact mass spectral analysis confirmed the structures of the esters and showed M+, (M — R)+, and (M – OR)+ ions containing the dioxaphosphocin ring system.
TL;DR: In this article, the reactions of octachlorocyclotetraphosphazatetraene, N4P4Cl8, with spermidine and spermine in a mixture of Et2O/MeCN (1:2) have been studied.
Abstract: The reactions of octachlorocyclotetraphosphazatetraene, N4P4Cl8, with spermidine and spermine in a mixture of Et2O/MeCN (1:2) have been studied. Spermidine gave two products. Both consisted of two tetramer units: in one they were linked by one spermidine residue, in the other by two. Spermine gave one product, two tetramer units linked by a spermine residue. All three products contained six-membered spiro moieties. Their 31P and 13C n.m.r. spectra are reported and compared with the products of the same two amines with hexachlorocyclotriphosphazatriene, N3P3Cl6.
TL;DR: The use of chiral sulfites for asymmetric synthesis of sulfoxides has been studied in this paper, where the authors discuss the various possibilities of using chiral sarsites for sulfoxide synthesis.
Abstract: Recent progress in asymmetric oxidation of sulfides is passed in review, and the various possibilities of using chiral sulfites for asymmetric synthesis of sulfoxides are discussed
TL;DR: The cyclic polysulfanes exo-3,4,5,6,7,8,9-heptathiatricyclo[9.2.1.02, 10]tetradecane (C7H10S7) and exo 3, 4, 5, 6, 7, 8, 9, 10-octathiatric yclo [10.2] have been prepared from the corresponding trisulfane C7H 10S3 by chlorination resulting in the two sulfenylchlorides C 7H10
Abstract: The cyclic polysulfanes exo-3,4,5,6,7,8,9-heptathiatricyclo[9.2. 1.02, 10]tetradecane (C7H10S7) and exo- 3,4,5,6,7,8,9,10-octathiatricyclo[10.2.1.02.11]-pentadecane (C7H10S3) have been prepared from the corresponding trisulfane C7H10S3 by chlorination resulting in the two sulfenylchlorides C7H10(SCI)2 and C7H10(SCI) (S2CI) which react with (C5H5)2TiS5 to yield the title compounds in good yields. Similarly, C7H10S5CI2 was obtained from C7H10S5 and Cl2 and yielded C7H10S10 on treatment with (C5H5)2TiS5. The hepta- and octasulfanes form pale-yellow microcrystals which have been characterized by UV, mass, Raman, and 1H NMR spectroscopy. The retention time of C7H10Sn molecules in reversed-phase HPLC is a function of the number of sulfur atoms (n = 3… 12).
TL;DR: In this article, a structural study using X-Ray Crystallography of the amino hydroxy diphosphonic acid of the title has been done, and the final objective is to use this functionalized hydroxy Diphosphoric acid in complexation study and in organic synthesis of biological derivatives by the way of amino group.
Abstract: Structural study using X-Ray Crystallography of the amino hydroxy diphosphonic acid of the title has been done. The final objective is to use this functionalized hydroxy diphosphonic acid in complexation study and in organic synthesis of biological derivatives by the way of the amino group. Results are discussed on the basis of the environment of phosphorus atoms and on the molecular geometry around the central carbon atom.
TL;DR: In this paper, the coordination geometry around bismuth is slightly distorted octahedral with three short and three long Bi[sbnd]S bonds (average lengths, 2.74 and 2.85 A, respectively); 1,3,2Dioxaphosphorinane rings are present in chair form.
Abstract: Bismuth tris(2,2-diethyltrimethylene dithiophosphate), M = 884.8, monoclinic, P2,/c, a = 9.591(3), b = 10.059(1), c = 36.170(5) A, β = 90.51(2)°, V = 3489.5 A3, Z = 4, Dc = 1.68 g cm−3, (MoKα) = 0.71069 A, μ = 55.5 cm−1, F(000) = 880, T = 295 K. Final R = 0.122 for 3183 reflections. The coordination geometry around bismuth is slightly distorted octahedral with three short and three long Bi[sbnd]S bonds (average lengths, 2.74 and 2.85 A, respectively); 1,3,2Dioxaphosphorinane rings are present in chair form. Preliminary data have also been obtained for bismuth tris(2,3-butylene dithiophosphate), M = 758.6, monoclinic, C2/c, a = 16.684(8), b = 13.682(6), c = 11.930(6) A, β = 98.45(2), V = 2693.8 A3, Z = 4, T = 295 K, Dc = 1.87 g cm−3,μ = 69.1 cm−1 and R = 0.052 for 1073 reflections. The chelation is symmetrical in this compound with Bi-S bond lengths of 2.76 and 2.79 A.
TL;DR: In this paper, 1, 3-thiazole-5(4H)-thiones with a vinyl substituent at C(4) are photochemically transformed into fused polycyclic compounds or, after C-alkylation to the corresponding 4, 5-dihydro-5-mercapto-1, 3 -thiazoles, via radical cyclization.
Abstract: Various 1,6-dithiaspiro heterocycles can be synthesized from 1,3-thiazole-5(4H) -thiones via 1,3-dipolar cycloadditions, Diels-Alder reactions, ring expansion of oxiranes, and C-alkenylation followed by radical cyclization. 1, 3-Thiazole-5(4H)-thiones with a vinyl substituent at C(4) are photochemically transformed into fused polycyclic compounds or, after C-alkylation to the corresponding 4,5-dihydro-5-mercapto-1,3-thiazoles, into fused bicyclic compounds via radical cyclization. With mCPBA, 1,3-thiazole-5(4H)-thiones are oxidized to thionoxides, which fail to undergo cycloaddition reactions.
TL;DR: In this article, the reaction of N-alkyl (or aryl) pyridine carboxamide oximes with thiophosgene was shown to yield 3,4 disubstituted 1,2,4-thiadiazole-5(4H)-ones.
Abstract: 3-Pyridyl-4-alkyl (or aryl)-1,2,4-oxadiazole-5(4H)-thiones are prepared by the reaction of N-alkyl (or aryl) pyridine carboxamide oximes with thiophosgene. Rearrangement, catalysed by metallic copper, yields the corresponding 3,4-disubstituted-1,2,4-thiadiazole-5(4H)-ones.
TL;DR: In this article, the Knoevenagel condensation of alkoxy/ carbamoyl benzylsulfonylacetic acid (V) and 4-carboxybenzyl sulfonylnyclic acid (VI) with araldehydes was used to obtain unsaturated sulfones.
Abstract: Novel unsaturated sulfones E-alkoxy/carbamoyl benzyl styryl sulfones (VI) and E-4(N-benzylcarbamoyl)benzyl styryl sulfones (IX) have been prepared by the Knoevenagel condensation of alkoxy/ carbamoyl benzylsulfonylacetic acid (V) and 4-carboxybenzylsulfonylacetic acid (VIII) with araldehydes. The E-geometry of these compounds has been assigned based on IR and 1H NMR spectral data.
TL;DR: In this paper, a Kernphos-phorylierung unter Abspaltung eines tert.-Butylrestes als Isobuten und Bildung von 13 bzw. 14 beobachtet.
Abstract: Durch Addition von Diethylphosphit bzw. Diphenylphosphinit an die 7,7-Bisphosphoryl-3,5-di-tert.- butyl-chinonmethide 5 bzw. 10a lassen sich geminale 4-Hydroxyarylmethan-trisphosphonate 6 bzw.- bisphosphono-phosphinoxide 11 gewinnen. Bei Versuchen, auf gleichen Wegen aus 10a bzw. 10b analoge Derivate mit einem Phosphono-und zwei Phosphinoxido-Resten (12) zu gewinnen, wurde Kernphos- phorylierung unter Abspaltung eines tert.-Butylrestes als Isobuten und Bildung von 13 bzw. 14 beobachtet. Gleiche Reaktion trat beim Versuch der Synthese eines gem. Tris-phosphinoxides aus 10b ein. Diese unerwartete Reaktion verlauft vermutlich analog einer von L. Horner aufgeklarten Kernphosphorylierung von Benzochinon mit Triphenylphosphin. By addition of diethylphosphite or diphenylphosphinite to the 7,7-bisphosphoryl-3,5-di-tert.-butyl-quinone methides 5 or 10a, the gem. 4-hydroxyarylmethane-trisphosphonate 6 or bisphosphono-phosphinoxide 11, resp., are formed. When we tried to prepare analogous derivatives with o...
TL;DR: In this article, N-benzyl-N-dihydroxyphosphonylmethyl-glycine (PHG) was used to debenzylate formaldehyde and phosphorous acid in 30% HCl-solution.
Abstract: Interaction of N-benzylglycine, formaldehyde and phosphorous acid in 30% HCl-solution produces N-benzyl-N-dihydroxyphosphonylmethyl-glycine 1, in 90% yield. Debenzylation of 1, dissolved in water with H2 in the presence of 5% Pd/C as catalyst gives glyphosate 2 in quantitative yield.