N-phenylglycine

Based on this observation, K. Heumann treated N-phenylglycine [103-01 -5] with alkali and obtained indoxyl (38) (keto form), which on aerial oxidation converted to indigotin ... 

A1( -octalone, 45, 80 N-nitioso-N-phenylglycine to N-phenylsydnone, 45, 96 Cyclobutanecarboxylic acid, reaction with hydrazoic acid, 47, 28 Cyclobutene, 1,2,3,4-tetrasiethyl-3,-4-dichloro-, 46, 34 reactions of, 46, 36 Cyclobutylamine, 47, 28 Cyclobutyl isocyanide, 46, 77 Cycloheptanone, 45, 31... 

Nitrosation, of amides with dinitrogen tetroxide, 47, 46 of N phenylglycine, 46, 96 p-Nitrosodimethylamhne, reaction with o nitrobenzylpyndimum bro mide, 46,82... 

N-Nitroso N phenylglycine, 46, 96 reaction with acetic anhydride to yield 3 phenylsydnone, 46, 96 Nitrosyl chloride, addition to bicyclo-[2 2 ljhepta 2,5 diene, 46, 75 2,4-Nonanedione, 47, 92 Nonane, 1,1,3 trichloro-, 46,104 Nortricyclanol, 46, 74 oxidation by chromic acid, 46, 78 Nortricyclanone, 46, 77 Nortncj clyl acetate 46, 74 frombicyclo[2 2 ljhepta 2,5 dieneand acetic acid, 46, 74 saponification of, 46, 75... 

N-phenylglycine org chem C8H5NHCH2COOH A crystalline compound, moderately soluble in water, melting at 127-128°C used in dye manufacture (indigo). en fen-arglT,sen )... 

B. 3-Phenylsydnone. The 99 g. (0.55 mole) of N-nitroso-N-phenylglycine is dissolved in 500 ml. of acetic anhydride in a 1-1. Erlenmeyer flask fitted with a reflux condenser topped by a drying tube. The deep-red solution is heated in a boiling water bath... 

This procedure is a modification of preparations of 3-phen)d, sydnone described earlier. The dehydration of N-nitroso-N phenylglycine has also been effected by the use of thionyl chloride and pyridine in dioxane, thionyl chloride in ethertrifluoroacetic anhydride in etherand diisopropylcarbodiimide in water or by reaction of the alkali metal salts of N-nitroso-N-phenylglycine with phosgene or benzenesulfonyl chloride in water or with acetyl chloride in benzene. ... 

Phenylsydnone is the prototype of that class of mesoionic compounds called sydnones. On acidic hydrolysis it produces phenylhydrazine, whereas basic hydrolysis regenerates N-nitroso-N-phenylglycine. This sydnone undergoes a variety of electrophilic substitutions, including mercuration and... 

Phenylethynylsilver, 46, 88 Phenyleth5mylsodimn, 46, 88 N-Phenylglycine, reaction with nitrous acid, 46, 96... 

This Norit treatment, when combined with the preceding filtration, does much to improve the purity of the N-nitroso-N-phenylglycine though the yield of nitroso compound thereby is lowered, the jdeld of the sydnone is increased correspondingly and the sydnone is much purer. 

Chloroacetamide derivatives such as N,N-diallyl (5) and N-alkoxymethyl-N-2,6-diethylphenyl (<5) analogs are widely used as upland field herbicides. By modification of chloroacetamide structure, Fujinami et al. found that the N-chloroacetyl-N-phenylglycine esters (7) show varying degrees of inhibitory activity, in particular, against shoot growth of annual grasses 17). They developed Eq. 15 and 16 for the herbicidal activities of various esters where the aromatic substituents are fixed... 

Other carboxylate-dye interactions have been reported. Ethylenediamine tetracarboxylic acid (EDTA) and its salts are well known reductants for a variety of dyes (54,55). The amino-acid N-phenylglycine can be photooxidized and induce polymer formation (26,56,57). Studies of the efficiency of photopolymerization of acrylate monomers by MB/N-phenylglycine combinations as a function of the pH of the medium suggest that either the amino group or the free carboxylate can act as an electron donor for the dye excited state, but that the amine functional-lity is the more efficient coinitiator (10). Davidson and coworkers (58) have shown that ketocarboxylic acids are photode-carboxylated by electron transfer quenching of dye triplet states under anaerobic conditions. Superoxide formation can occur when oxygen is present. 

Values listed for relative photospeeds in film-based media are from our own work (64,65), as are the solution data for N-phenylglycine (NPG) and tri(n-butyl stannane (TBBS). Film and solution data can not be directly compared (but see below). 

N-Phenylglycine in the form of an alkali metal salt (11) is the starting material for the Heumann I synthesis. It can be prepared in various ways [15] (Scheme 2). 

The reduction of benzylideneanilines in aprotic electrolytes in the presence of C02 can be used for the synthesis of N-phenylglycines 492 496) ... 

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