Reduction of Nitroguanidine. V. The Synthesis of (a) α-Methyl-, (b) α-Ethyl-, (c) α-n-Butyl-γ-aminoguanidine¹

Abstract

A --33,700 (oxygen ring left) (The value of A for /3-d-glucosidodihydroxyacetone pentaacetate may be derived from its rotation of [«]18d -25.2°r eported by Kreider and Evans.4) The above numerical values of A agree among themselves very closely when it is remembered that the Van't Hoff rule of optical superposition on which these calculations are based is known to be only approximate in its quantitative predictions. These values tend to substantiate the structure ascribed to the new compounds reported in the experimental part of this paper.

1,1′-Diamino-5,5′-azotetrazole: a nitrogen rich compound

“…1), which contain bulky organic species, a phenyl group, and a butyl group. [15][16][17][18][19][20][21][22] In addition, the small methyl group decreases the possibility of hydrogen bond forming. In contrast, 1 has a higher nitrogen content (85.7%) and more hydrogen bonds.…”

The synthesis of certain 5-aminotetrazole derivatives. II. The action of hydrazoic acid on monoalkylcyanamides

“…After allowing the solvent to evaporate 20 g. of crude colorless product remained from which no acidic material was extracted by cold aqueous alkali. The crude material gave 12 g. of fine, colorless needles after one crystallization from water. The product was identical in all respects with a sample of l-methyl-5-ammotetrazole prepared according to von Braun and Keller (3).…”

Oxidative cyclization of carbonyl derivatives. 5-Imino-Δ1-1,2,4-triazolines from alkylideneimino guanidines

“…-1,2,4-frinzoli~res (46 nrrd tile E Isor~rer') Acetone-4-phenylthiosemicarbazone (5) (13) was methylated by a procedure modelled after Kirsten and Smith's methylation of thioureas (14). T o an ice-cold solution of 5 (21 g, 0.1 mol) in 200 ml of absolute ethanol was added methyl iodide (15 g, 0.1 mol) a n d the resulting solution was stirred for 3 h at ice temperature and subsequently for 12 h at room temperature.…”