140 REPORT OF SCHIMMEL & Co. APRIL 1914. 
camphor in the preparation of sulphuryl chloride by Schulze’s method (reaction of 
chlorine with sulphur dioxide in the presence of camphor). The authors have come 
to the conclusion that in this reaction camphor does not act as a catalyst, but that 
the compounds 2 SO2-CioHigO, m.p. — 45° and SO2-CioHigO, m.p. — 24° are formed 
as intermediary products, and that these on their part react with chlorine. 
B.L. Vanzetti') has ascertained that the absence of all thermic effect when the 
dilute solutions of the two active forms of the camphor oximes, which constitute a 
true racemate, are mixed together. He has thereby proved that in dilute solutions the — 
racemate has become completely decomposed into the two optical antipodes. 
Epicamphor. On p. 159 of our Report of October 1912 we referred to a paper on 
the preparation and properties of epicamphor, by J. Bredt and W. H. Perkin, published 
in the Proceedings of the Chemical Society. Since then the authors have published the 
experimental details of this investigation in other journals”), which fact enables us to 
complete our reference by the following particulars: — 
The preparation of epicamphor may start with d-bornylene-3-carboxylic acid, which 
is converted from its primarily-produced chloride into the hydrazide and the azide. 
The last-named, when boiled with hydrochloric acid, affords /-epicamphor. A drawback 
of this method is the danger of explosion with which the preparation of the azide is. 
attended. The preparation of epicamphor from d-bornylene-3-hydroxamic acid is there- 
fore to be preferred. When heated above its melting-point the hydroxamic acid, with 
explosive rapidity, forms epicamphor, ammonia, water and a yellow-coloured resin. 
The mechanism of this reaction is probably as follows: bornylene-3-hydroxamic acid, 
when heated, loses water, and at the same time a molecular transposition takes place 
with formation of a resinous product consisting of bornylene-3-isocyanate. The water 
which has been formed in the course of the reaction splits up part of the isocyanate 
into ammonia and epicamphor. When the resin is treated with hydrochloric acid and 
distilled with steam, epicamphor is obtained by this method. The decomposition of 
acetyl- and benzoyl-d-bornylenehydroxamic acid is attended with less violence. When 
treated with toluene-p-sulphochloride these derivatives undergo transposition in the 
manner described under bornylenehydroxamic acid, giving rise to /-epicamphor. Un- 
fortunately the preparation of d-bornylene-3-carboxylic acid takes a great deal of time 
and is very complicated, and epicamphor therefore remains a preparation which it is 
difficult to obtain. J-Epicamphor has the following characters: m.p. 182°, b. p. 213°, 
[@]) — 58,21° (in benzene). 
Singularly enough, the /-epiborneol which is formed in the process of reduction 
of J-epicamphor has no optical rotation. It is nevertheless no inactive substance, 
for it may be converted into /-bornylene (#p) — 18,45°) from the primarily-produced 
xanthogenate. 
Epicsoborneol corresponding to isoborneol is as yet unknown. 
Epicamphor is no more capable than common camphor of forming a cyanohydrin. 
Epicamphocarboxylic acid is more readily reducible than is camphocarboxylic acid. 
Even when treated with sodium amalgam reduction takes place, although but slowly. 
By the electrolytic method’) reduction proceeds readily, with formation of four isomeric 
l-epiborneolcarboxylic acids, which differ from each other in their m.p. and their 
1) Atti R. Accad. dei Lincei, Roma V. 22 (1913), II. 379; Chem. Zentralbl. 1914 I. 145. — 7) Journ. chem. 
Soc. 103 (1913), 2182. Journ. f. prakt. Chem. Il. 89 (1914), 209. — 3%) Comp. Report April 1912, 191. 
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