125 
 Bietoré Bene Nag Wat. ‘the: details oF vist aK: we Papiah to state. that the terms 
- and ‘@-fenchene- were used by Komppa and Roschier'). They termed Wallach’s 
D, ), -fenchene, nS a-fenchene” and his D,d-fenchene, “d,@-fenchene”, and the racemic 
fe orm. ‘of this hydrocarbon, “ d, i-8-fenchene”. _ Although Wallach’s terms have hitherto 
been ‘universally. used in. the literature, they give rise to ‘difficulties when it is the 
“suggested the new names. 
pure D, Lfenchyl alcohol. resulted. M. p. 46.5 to 479; b. p. 201 to 202°. [2]p - — 12.93°. 
: Tn the same manner, E; d-fenchyl alcohol was obtained from the oxalate (m. p. 92 to 93°). 
From the racemic mixture of the oxalates, Qvist prepared, by saponification-racemic 
“fenchyl alcohol; m. p. 35.5 to 379; b. p. 200 to 201° (755 mm.).. 
peesisonatty more lower-boiling hydrocarbons than the former. 
From D,l-fenchyl alcohol, Qvist obtained, by heating with KHSO, in a imeiattie 
bath up to 200°, a mixture of hydrocarbons boiling between 139 and 157° (759 mm.). 
| known, the following structural formula applies to isofenchylene: cua ee 
scapes “octace Nan © 5 CERcae ge eee EY CH at 
ES) Sea Sccih)s fC yCiCtide 2 
, | Che ; aie Wh CH,» | . 
ABOLC Ron es Hel | olen, ‘ 
rete Mie oe a Se CH 
d, U-Isofenchoic acid (Isofenchocamphoric eer _ Tsofenchylene. 
_ to isofenchyl alcohol, as with bornylene and borneol. 
_with KMnO, d-hydroxy-é-fenchenic acid (D, d-hydroxyfenchenic acid). The parts not 
attacked by KMnO;, contained cyclofenchene, b. p. 141.5 to 142° (755 mm.). 
 Qvist prepared furthermore fenchenes from fenchyl alcohol by the xanthate method, 
x 
ee AP) Aeighi. Acad. Scient. Fenn., ‘Seri A F- (1916), No. 14; Chem. Zentralbl. 4917, | 407. — 2) Journ. chem. Soc. 78 
(1898), 276. — *) Comp. Wallach, Liebig’s Annalen 362 (1908), 184; Report November 1908, 190. — *) Comp. Aschan, 
 Whebig’s Annalen 387 (1912), 51; Feport April 1908, 179. — Sandelin, Liebig’s Annalen 896 (1913), 315; Report October 
1913, 149. — °%) Journ. Russ. phys.-chem. Soc. 48 (1916), 450; Report October 1917, 146. — °) Annal. Acad. Scient. 
Foun, Ser. A, 8.(1917), No. 15, p.5; Se October 1918, Apr *) Chem. Ztg. 28 (1899), 1061; Report April 1900, 54. 
. Pa, ae iP ' , ; / 
ase of inactive fenchenes, and this | was. the reason why Komppa and Roschier 
Firstly, Qvist reports on fenchenes plepared roth: fenchyl alcohol, which was — 
Sobiained: from D-fenchene by reduction. Wallach’s: method — reduction with sodium - © 
in ethyl alcoholic solution — did not give the good yield as did the process of — 
3 Gardner and Cockburn”) (sodium and amyl alcohol). In order to obtain a quite pure © at 
"preparation, Qvist transformed the alcohol into its oxalate (m. p. 92.5 to 93.59) by a 
heating” it for 5 hours to 125° with oxalic acid; on ‘saponification of the oxalate, the 
A fraction boiling from 141 to 143°, contained J, a-fenchene, which was. proved, inter | 
alia, by oxidation to I-hydroxy-a-fenchenic acid *). Likewise, isofenchylene was present 
‘in this fraction, on oxidation with potassium permanganate that hydrocarbon yielded 
 cis-d, L-isofenchoic acid*) (isofenchocamphoric acid). ithe constitution of. this. acid being mn 
; Isofenchylene - -is identical with the’ fenchylene of Nametkin and Rucnencevan 
obtained by the xanthate method. Equally, the hydrocarbon prepared by Komppa 
and Roschier®) and termed by them d-fenchene or isofenchene, is identical with iso- 
_fenchylene. _ Qvist adopts this name since it reveals the relation of the hydrocarbon ae 
The fraction of b. p. 152 to 155° contained d, 6-fenchene and yielded ‘on. oxidation ‘ 
2 par is formerly made use of Py us and by Tehugaeti wt however, with less favourable | 
Direct abstraction of water from fenchyl alcohol was ‘most readily effected byiee : 
4 heating with aluminium phosphate or potassium hydrogen sulphate; the latter "yielding 
