CLVI.—Hydroxyoxamides. Part II

Robert Howson Pickard, Charles Allen, William Audley Bowdler, William Carter
1902 Journal of the Chemical Society Transactions  
SCHIFF AND MONS ACCHI (Anncclen, 1895, 288, 31 3) hydrolysed oxamethane with hydroxylamine, and obtained a compoand to which they gave the name " hydroxylamide," and ascribed the formula, NH,*CO*CO*NH*OH. At the same time, they pointed out t h a t it decomposed at the same temperature as, and was very similar to, t h e compound obtained by Holleman (Rec. truv. chim., 1894, 13, 84) by the action of hydrochloric acid on oxamidedioxime. Holleman then compared the two substances (Rec. trav. chim.,
more » ... (Rec. trav. chim., 1896, 15, 148) , showed t h a t they were not identical, and suggested t h a t they were stereoisomerides of the formula NH,*C(NOH)*CO*OH. H e gave the syn-formula t o his own compound, since this more readily explains the formation of cyanamide when it is treated with acetic anhydride. The anti-configuration was given t o Schiff and Monsacchi's compound, as this more readily accounts for the formation of carbon dioxide and carbamide when it is heated. I n 1901, it was shown by Pickard and Carter (Trans., 79, 841) t h a t
doi:10.1039/ct9028101563 fatcat:3sytoqibdzbohh5fdeauiyqpzi