Henry Feuer

The infrared spectra of the salts of nitro compounds. Characteristic frequencies of the carbonitronate group, CNO2−

Abstract The infrared spectra of salts of nitro compounds have been studied and the N-O asymmetric and symmetric stretchings of the carbonitronate ion have been assigned to the regions 1316–1205 and 1175–1040 cm−1. The CN frequency of sodium alkanenitronates appears in the region 1605–1587 cm−1. The carbonyl and the nitrile stretching frequencies in α-nitroketones and α-nitronitriles are considerably reduced due to conjugation with the carbonitronate group.

The Michael reaction of enamines with nitroolefins

Abstract Several Michael reactions of enamines with nitroolefins (or their cogeners, the β-nitroalkyl acetates) are described. Reduction of the products with amalgamated aluminum leads to heterocyclic compounds, e.g. from 2-(β-nitro-α-phenylethyl)cyclohexanone (IV) to a partially hydrogenated 3-phenylindole (VII).

Methylolation of α; ω-dinitroalkanes

Abstract The sodium hydroxide catalyzed methylolation of 1,4-dinitrobutane (I) has been found to yield 2,5-dinitro-1,6-hexanediol, (IV; both epimers), and 2,5-bis-hydroxymethyl-2,5-dinitro-1,6-hexanediol (II). No evidence was obtained for the formation of the unsym-metrical diol, 1,1-bis-hydroxymethyl-1,4-dinitrobutane (VI) or the triol (VII). Methylolation of I bis-nitronate ion led to IV and 2,5-dinitro-1-pentanol (V). Similarly, 2,6-dinitro-1-hexanol (X) and 2,6-dinitro-1,7-heptanediol (XI, both epimers) have been prepared from 1,5-dinitropentane.

Proton exchange and hydrogen bonding in hydroxylamine derivatives

Abstract Proton exchange in hydroxylamines, RNHOH, has been investigated by nuclear magnetic resonance spectroscopy. Hydrogen bonding of the hydroxylamines and their N,N-and N,O-disubstituted derivatives by self-association as well as by their interaction with electron donors has been studied by nuclear magnetic resonance and infrared spectroscopy. The results indicate that the OH group participates to a greater extent in hydrogen bonding than the NH group. The O-H⋯Y (Y = donor site) hydrogen bonds are found to be generally stronger than the N-H⋯Y bonds.