; ete a now been nel by Aschan’). These acohOr are pita iso-- +33 
~ meric bodies in the same proportion as borneol and isoborneol. Methylcamphenilol 
~ results through the action of magnesium methyl iodide on camphenilone, where no — 
_ transposition is to be supposed. As the constitution of camphenilone is established, 
_ to methylcamphenilol the structure given in the formula hereafter would be due. 
_ Camphene hydrate forms already at 60° through the action of milk of lime on camphene — 2% 
~ hydrochloride. When camphene, which contrary to former suppositions is uniform‘), 
z hes up hydrogen chloride, no transposition takes place. Aschan already previously 
succeeded in proving this, by transforming a dextrorotatory camphene first into its 
_ levorotatory hydrochloride and then through stirring with alkali into a feebly rotatory _ 
__ camphene hydrate, from which he recovered the camphene, possessing the original ae 
_ rotation, by slightly splitting off water. Furthermore, a camphene hydrochloride of 
x unaltered rotation was recovered, if it was first transformed into camphene hydrate ee 
E- and regenerated with the aid of hydrogen chloride. Hence it is evident that camphene — Bet 
Bp ydrate forms without any transposition of the original camphene skeleton and there 
fore is a true derivative of camphene. Starting from Wagner’s camphene formula, — A 
a CH | CH =. 
Ha" | CCH) Hic) CIC eo 
. Cl OH- =e 
: VA : Ry 
pees cc HC™. |, eae hae 
: Camphene. ; Camphene hydrochloride. Camphene hydrate. = ; = 
one arrives at the structure of the camphene hydrochloride as well as of the hydrate. : = 
_ The formula for the latter coincides in structure with that of methylcamphenilol. The 
_ two bodies are not identical, however, for they differ in their melting points, their 
a _ boiling points and in the boiling points of their phenylurethanes, as shown hereafter: | 
5 Methylcamphenilol ...... -. mp. 117 to 1189, b.p. 204 to 206° eas ag 
== Camphene hydrate ....... mp. 150 to 151°, b.p. 206 to 207,5° ae 
ee Methylcamphenilol phenylurethane m.p. 126° — eer. 
a Camphene hydrate phenylurethane m.p. 89°. : . = 
a : In consequence, it must be a case of stereometric isomerism, as expressed by the Se 
formulas 3 Pt 
ee: | oo mh ee 
= Hic] (CH Be ce 3 
s c | 2 OH H c! | 2 CS CHs a 
esr eas.“ CH, es ee OH & 
CH Cis fee 
Methylcamphenilol and camphene hydrate. <a “3 
1) See Report October 1904, 111; April 1905, 91; October 1905, 104. — 7) See Report October 1911, asad 
132. — : Liebigs Annalen 410° (1915), 202. — *) See A. Hesse, Berl. Berichte 89 (1906), 1127; Report October - 
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