LXXXVI.—The action of magnesium methyl iodide on pinene nitrosochloride

William Augustus Tilden, Joseph Arthur Stokes
1905 Journal of the Chemical Society Transactions  
WITH the object of further studying pinene nitrosochloride and the circumstances in which the nitroso-derivatives of pinene retain the bimolecular constitution, it was thought that some interest would attach t o the replacement of the chlorine of the nitrosochloride by an alkyl group. For this purpose, the use of Grignard's reagent at once suggested itself, and the anticipated reaction has been accomplished. The resulting oxime possesses well developed basic properties, as it readily forms a
more » ... ble hydrochloride. The proportions of materials employed and the conditions of experiment have been varied in successive operations, but the yield of the oxime remains very small, amounting to less than 10 per cent. of the nitrosochloride used. The by-products are chiefly uncrystallisable and become brown on exposure to the air. They include, however, a notable quantity of a n interesting saturated base produced by the interaction of the magnesium alkyl iodide with the oxygen of the nitroso-group, the chlorine of the nitrosochloride remaining undisturbed. The products are represented by the following formulas : Pinene nitrosochloride. Me thy lpinoneoxime. Bimolecular. Unimolecular. The saturated base, chlorhydrodimethylpiny lainine. Unimolccnlar, 193O.
doi:10.1039/ct9058700836 fatcat:hl27d3hbfnaudfnu5vkopyy7ve