ON HYDRO-AROMATIC COMPOUNDS WITH SINGLE NUCLEUS. 125 



two active modifications, its occurrence in optically active forms being 

 satisfactorily explained by Baeyer's suggestions, > which would suppose 

 the hydroxyl groups to occupy different positions relatively to the plane 

 of the hexamethylene ring. The inactive variety occurs in muscle,- &c., 

 and as its monomethyl ether (bornesite), CcHs(0H)5 . OCH3, and dimethyl 

 ether (dambosite) in caoutchouc.^ c?-Inosite and Mnosite are obtained 

 from their monomethyl ethers, respectively pinite ^ and quabrachite,'^ by 

 the action of hydriodic acid. 



The constitution of inosite results from the work of Maquenne/' who 

 suggested the formula ^ 



.CH(0H).CH.OH 

 CH.OH NcH.OH 



\CH(0H).CH.0H 



It gives a hexacetate ; ^ with hydriodic acid yields benzene and triodo- 

 phenol ; is oxidised completely to carbon dioxide by potassium per- 

 manganate ; and with nitric acid gives the same oxidation products as 

 liexahydroxybenzene, namely, di- and tetra-hydroxyquinone. 



Hydroxytetrahydrobenzene is formed when 1 : 4-iodohydroxyhexa- 

 bydrobenzene (p. 123) is treated with quinoline.^ 



.CH„ . CH, ^CH . CH3 



CHI \CH . OH CH \CH . OH 



\cHj . OH.. ^CH, . CH. 



Amines. 



Hydro-aromatic amines result from the reduction of the corresponding 



oximes. 



Aminohexahydrohenzene, CgHn . NHj, obtained as above,' « or by 

 reducing nitrohexahydrobenzene with tin and hydrochloric acid,'^ is a 

 colourless liquid smelling like conine. 



1:2- Diaminohexahijdrobenzene,^'^ 1:3- diaminohexahydrobenzene,^^ 

 1 : 'i-diaininohexahydrobenzene,^^ tetrahydrobenzijlamine.^'' 



Ketones. 



Ketohexahydrobenzene (pimeloketone) has been obtained (i.) by the 

 oxidation of hydroxyhexahydrobenzene,"^ (ii.) by the distillation of calcium 

 pimelate with lime,'^ 



.CH, . CH. . COOH xCH, . CH, 



CH, CH, \C0 



\CH., . CH.. . COOH \CH, . CH, 



' Annalcn, 1888, 245, 128. = Beilsteln, 3" Avfl., i. 1050. 



' Girard, Zeit.fdr Chem., 1871, :535. 



' Maquenne, Compt. Rend., 181)0, 109, 968. 



" Tanret, Compt. Rend., 109, 908. " Compt. Bend., 1887, 104, 225. 



' IMd., p. 297. " ^*i'^-. P- 1719- 



» Baeyer, AmiaUn, 1894, 278, 97. '° Baeyer, Ihid., 103. 



" MarkownikofE, Annalcn, 1898, 302, 22. '- Annalen, 1897, 295, 187. 



" Ibid., 1885, 228, 39. " Bcr., 1804, 27, 1449. 

 '^ J.C.S., \90l,Abstr.,i. 691. 



19 Baeyer, Annalen, 1894, 278, 107. " Baeyer, ibid. 



