The aryl thiazolidones studied correspond to the 2-arylamino or stable forms of Wheeler and Johnson.Their sodium salts with methyl or ethyl iodide yield a mixture of 2alkyl-2-aryl and of 3-alkyl-2-aryl thiazolidones. With benzyl chloride only the 2-benzyl derivative has been found.These results have failed to confirm the formulation of Beckurts and Frerich, who assumed that the products they obtained were 2-alkylimino-3-aryl thiazolidones. Further unpublished investigations in this Laboratory support our experimental results.

The work reported in this paper is part of a unification of effort by a number of agencies having responsibility for the solution of the problem of drug addiction.

the presence of the enol ether group. When dihydrothebaine is extracted from a Soxhlet apparatus into boiling ethereal methylmagnesium iodide an addition compound slowly separates, and at the end of five days no more dihydrothebaine can be detected. The product consists principally of a

When thebaine (I), in glacial acetic acid solution, is treated with hydrogen peroxide1 the ketone, hydroxycodeinone, of the generally accepted2 •3 structure II is formed. The process apparently involves a 1,4-addition reaction, with the equivalent of hydrolysis at the enol ether group of thebaine, whereby a tertiary alcoholic hydroxyl appears at C-14, and a carbonyl group at C-6 in the end product. The position of the carbonyl group and the existence of the intact morphine skeleton in hydroxycodeinone seem well established by the facts that bromocodeinone (III) can be transformed to hydroxycodeinone oxime through the action of hydroxylamine, and can also, by reductive elimination of bromine, be converted to the well known morphine derivatives codeinone (IV)2'4 and dihydrocodeinone.6 The only structural features of hydroxycodeinone involving any uncertainty beyond that inherent in the morphine formula, are the locations of the alicyclic unsaturation and of the alcoholic hydroxyl group. (See p. 221.) The hydroxycodeinone formula originally advanced by Freund and Speyer represented the hydroxyl as occupying C-7, and since the group has not the properties of an enolic hydroxyl, this necessitated locating the unsaturation between C-8 and C-14. As Robinson has pointed out, hydroxycodeinone does not behave like an -hydroxy ketone, nor do the results of cyanogen bromide degradation1 • 6point to location of the double * The work reported in this paper is part of a unification of effort by a numbr of agencies having responsibility for the solution of the problem of drug addiction. The organizations taking part are: The Rockefeller Foundation, the Nati on a Research Council, the U.

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