collaborators, more or less continuously from the year 1880 down t o the present time, has been the synthesis of cycloids. The various " condensations i n the ortho series " which, shortly before this work was begun, had been studied by various investigators, especially by Ladenburg and von Baeyer, indicated a possibility of the occurrence of similar condensations in the case of aliphatic chains containing two ketonic or alcoholic functions in the a-position. I n passing, we may point out that the analogy of the a-position in aliphatic compounds to the ortho-position in the benzene series was not quite so obvious then as it is now. A t that time, Ladenburg's '' prism '' formula could still be seriously put forward as a satisfactory expression of the reactions of benzene ; and in this formula the ortho-carbon atoms are not directly united. Every condensation, therefore, which bore out the foregoing analogy was a fresh argument against the '' prism " formula. Indeed, it is cumulative evidence of this character, rather than any definite disproof, that has caused the '' prism " formula to be withdrawn from discussion. The a-diketones and the a-keto-alcohol just mentioned were selected for study, in the first instance, on account of the ease with which they could be obtained. A further advantage was that the products of the various reactions were crystalline solids and, consequently, easy to purify. The phenyl and phenylene groups, to the presence of which in the molecule the latter advantage was largely due, took no direct part in the reactions ; so that, in reality, the problem resolved itself into the relatively simple one of ascertaining the nature of the condensations of the groups-CO*COand-CHOH* GOwith various compounds. Against these advantages must be set the deterrent effect which the somewhat formidable-looking formulae of the resulting compounds probably exercised on the majority of readers. That this object of the synthesis of cycloids has been amply realised may be seen from the following list of the various classes of compounds obtained in these reactions :
DRY silver oxide and alkyl iodides have been employed as a n alkylating agent, by Purdie and Pitkeathly, in the preparation of nlkyloxyand dialkyloxy-succinic esters from malic and tartaric esters (Trans., 1899, 75, 157), by Purdie and Irvine in the preparation of a-alkyloxypropionic esters from lactic esters (Trans., 1899, 75, 485), and by McKenzie in the preparation of alkyloxyphenylacetic esters from mandelic esters (Trans., 1899, 75, 754).Apparently, the only prior applications of dry silver oxide as a synthetical agent are its use by Wurtz in the formation of ethyl ether from ethyl iodide (Ann.Chim.
IT seemed possible that when pure dry hydrogen iodide acts on the imidechloride of benzanilide, replacement of the chlorine atom by iodine might occur, and t h a t the resulting imide-iodide would then lose iodine and yield the dianil of benzil, thus : PhCC1:NPh + HI = PhC1:NPh + HC1 and 2PhCI:NPh = (PhC:NPh), + I,.We find, however, t h a t hydrogen iodide yields a n additive compound with the imidechloride, t o which we are inclined, although direct experimental evidence is wanting, t o ascribe t h e constitution of a mixed amide halide, in this case the chloroiodide corresponding mit,h benzanilide, PhCC1:NPh + HI = PhCClI*NHPh.Action of Hydrogen Iodide on Benxo~~iienylimidechloride.
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