. Annual report on essential oils, synthetic perfumes, &c. Essences and essential oils; Perfumes. CH Tricyclene dibromide (?) (constitution not yet certain). A complete elucidation of the above-mentioned transformation was obtained by the treatment of tricyclene and of camphene with gaseous hydrochloric acid. Both these compounds yielded then, the true, so far unknown, camphene hydrochloride (m. p. 125 to 127°), the chloride of Aschan's camphene hydrate2). The camphene hydrochloride is, as a tertiary chloride, characterised by the high mobility of the chlorine atom and by the ease with whi
. Annual report on essential oils, synthetic perfumes, &c. Essences and essential oils; Perfumes. CH Tricyclene dibromide (?) (constitution not yet certain). A complete elucidation of the above-mentioned transformation was obtained by the treatment of tricyclene and of camphene with gaseous hydrochloric acid. Both these compounds yielded then, the true, so far unknown, camphene hydrochloride (m. p. 125 to 127°), the chloride of Aschan's camphene hydrate2). The camphene hydrochloride is, as a tertiary chloride, characterised by the high mobility of the chlorine atom and by the ease with which hydrochloric acid is split off and camphene is formed. The low stability of the chloride is connected with this fact. In storing, the hydrochloric acid liberated by scission effects a gradual transformation of the camphene hydrochloride into isobornyl chloride (m. p. 158°, IV). The same process takes place rapidly when camphene hydrochloride is heated to 130 or 140° in a sealed tube, or when it is digested with methylalcoholic or ethereal hydrochloric acid at ordinary temperature. For this reason the so-far applied method of preparing camphene hydrochloride — saturation of the concentrated ethereal or alcoholic solution of camphene with hydrochloric acid and recrystallisation of the resulting product from a methyl- alcohol solution of hydrochloric acid — could only lead to an tsobornyl chloride containing camphene hydrochloride. We further understand why the literature records H2C CH C(CH3)2 H2C CH C(CH3)2 H2C CH C(CH3) HC CH2 I HC1 CCH; CH5 H2C HC1 C< CH< CH Tricyclene. ,2V-\L-—-CI CH Camphene H2C CH CH2 H2C CH C(CH3)2 HC- CH3C- CH3 C-CHa or CH9 CH HC CCH3 CH (I) Tricyclene. H2C CH CH2 H2C CH C(CH3)2 H2C CH CH2 C(CH3)2 CH2 H2G^J^_^C< H2C C^CH3 CH (II) Compound with bivalent carbon (III) Isocamphane atom, not capable of existence. CHCHj C(CH3)2 H2C^J^^CHC1 ^C-CH3 (IV) Jsobornylchloride. *) The constitution of this dibromide is not quite cert
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