Derivatives of isocamphoric acid, decomposition of isodihydroaminocampholytic acid with nitrous acid . mide it is evident that after the saponification of the ester an inver-sion occurred on the secondary asymmetric carbon, and that the sub-sequent loss of water formed the imide. Noyes and Knight reported an anhydride of the free isodihydro-aminocampholytic acid, and a peculiar nitroso-derivative of thisanhydride. The free acid was prepared by the writer; it was found tohave the following constants: m. p. - 235 - 236°; ( - °. The hydrochloride gives the following constants: m. p. - 296 -2
Derivatives of isocamphoric acid, decomposition of isodihydroaminocampholytic acid with nitrous acid . mide it is evident that after the saponification of the ester an inver-sion occurred on the secondary asymmetric carbon, and that the sub-sequent loss of water formed the imide. Noyes and Knight reported an anhydride of the free isodihydro-aminocampholytic acid, and a peculiar nitroso-derivative of thisanhydride. The free acid was prepared by the writer; it was found tohave the following constants: m. p. - 235 - 236°; ( - °. The hydrochloride gives the following constants: m. p. - 296 -29# with decomposition, ( °< )^9° = -4 °. It will be noted thatthe hydrochloride and the free acid have the same sign of same is true of dihydroaminocampholytic acid ( - °) and its hydrochloride ( ( o< ) - 42 .4° ) . For aminocamphonanic acii D O o ( ( <*) D ? and its hydrochloride ( ( °( )q - + , how- ever, the reverse is true. According to a view expressed by Noyes1 and Potter this means that aminocamphonanic acid forms an intra-molecular salt, thus:. 1. thesis, R .S. Potter (1913) ® while dihydroaminocampholytic acid does not. According to thisview the free isodihydroaminocampholytic acid will not form an in-tra-molecular salt in solution. This is to be expected from thefact that it is a trans-acid. There remains, though, the possibil-ity of an intermolecular salt in solution. Such a salt formationis indicated by the molecular weight of the acid in solution. Tworather accurate molecular weight determinations gave 190, and 192respectively as against 173 for the theory. Attempts to prepare the anhydride by distilling the hydrochlo- 1 ride with lime were unsuccessful. Potter and Noyes prepared theanhydride of dihydroaminocampholytic acid by warming with aceticanhydride. This method was used by the writer to prepare the an-hydride of isodihydroaminocampholytic acid. The anhydride did notform readily, but upon boiling for a half
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Keywords: ., bookcentury1900, bookdecade1910, booksubjecttheses, bookyear1913
