ChemInform Abstract: A New Route to Nitrile Oxides via α-Nitroso-diazo Derivatives.

ChemInform Abstract

Nitrile oxides, substituted with P-containing groups, were hitherto unknown. Therefore the reaction of nitrosyl chloride (IV) with the phosphonic acid derivative (III) is investigated, which leads to the P-substituted nitrile oxide (V) via an unstable diazo-α-nitroso derivative. The behavior of (V) in chemical reactions is typical for nitriles. Starting with (I) the attempt to prepare the diazo-α-nitroso precursor was not successful. This intermediate as well as the desired nitrile oxide are unstable, the latter one is converted into (IX) presumably by shift of the oxygen. (XI) is formed probably via oxidation of (I) followed by reaction with a second mole of (IV). Nitrile oxides were so far prepared only from organic compounds with C-N-O moieties. The conversion of compounds containing CN-single-, -double- or -triple-bonds in nitrile oxides or the introduction of a NO group in organic compounds with direct formation of such species was hitherto completely unknown.