104 REPORT OF SCHIMMEL g pal OeronER: 1914/A 
obtained. It is remarkable that on ozonization isoeugenyl acetate takes up more > oxy ger pone 
than what corresponds to its normal degree of saturation. Cok 
Normal eugenol ozonide, described already by Riedl von Riedenstein’), explodes 
much more easily than isoeugenol ozonide. It was reduced with zinc dust and afforded. 
a good yield of homovanillin (b. p. 111 to 114° at 0,45 mm.), a body of vanilla odour. 
The p-nitrophenylhydrazone melts at 150°; the semicarbazone, at 173° and the oxime, 
at 115°. On being shaken with sodium disulphite solution, homovanillin affords a 
sparingly soluble, white, powdery double compound which, however, has not a normal 
composition. 
Eugenyl acetate forms, contrary to isoeugenyl acetate, a normal ozonide. On 
fission with glacial acetic acid, it yields acetohomovanillic acid (m. p. 134°) and most 
likely acetylhomovanillin too. _ , | 
On fission of methyleugenol ozonide*) with glacial acetic acid, methylvanillin | 
results, the p-nitrophenylhydrazone of which melts at 210°. 7 
The reduction of methyleugenol ozonide can be carried out in the same way as “q 
that of eugenol or isoeugenol ozonides. Methylhomovanillin is then formed, which is 
characterized by a p-nitrophenylhydrazone melting at 157° and a semicarbazone melting 
at 181°. 
Safrole. We may here discuss a few derivatives of safrole and isosafrole out of 
a series described by R. P. Foulds and R. Robinson®). 6-Nitrosafrole is obtained by 
nitration of safrole dissolved in acetic acid; m.p. 25°. It is oxidized with potassium 
permanganate in acetone to 6-nitropiperonylacetic acid (m. p. 183°). The reduction of 
nitrosafrole with tin and hydrochloric acid leads to 6-aminosafrole (b. p. 168° at 15 mm.). 
Safroleazo-8-naphthol (m. p. 166 to 167°) results from safrolediazonium chloride and 
8-naphthol. 
Isosafrole in chloroform yields with bromine in excess bromoisosafroledibromide 
with one bromine atom in the ring, whereas in carbon disulphide isosafroledibromide 
is formed in the normal way. On distillation under reduced pressure it decomposes 
into hydrogen bromide and bromoisosafrole. When bromoisosafrole is heated with 
methyl! alcohol and potassium hydroxide, piperonylallylene is formed; m. p. 42 to 43°; 
b. p. 141°. 
Isosafrole. It is known that there are two modifications of isosafrole, named «- and 
8-isosafrole*) and distinguished from one another only by their physical properties. 
M. Mayer’®) purified S-isosafrole by way of the picrate (m.p. 75°). It boils at 250° and | 
can be converted into two polymerides (m.p. 95 and 150°, respectively), described | 
by us as well as by Puxeddu, Angeli and Mola®). Mayer examined the spectro-chemical , 
behaviour of both polymerides in the ultraviolet region. Both showed a very constant | 
absorption line in ultraviolet, beginning at 340 uw“. The spectroscopical behaviour of 
either isomeride indicates that they have the same molecular structure. 
Buchu camphor. G. Cusmano and P. Poccianti’) describe the conversion of dibromo- 
tetrahydrocarvone into buchu camphor. They prepared tetrahydrocarvone, following - 
1) Inaug.-Dissert., Kiel 1911. — *) Comp. R. Majima, Berl. Berichte 42 (1909), 3605. — #%) Journ. chem. — 
Soc. 105 (1914), 1963; Chem. Zentralbl. 1914, Il. 1188. — *) Comp. Report April 1910, 186. — 5) Atti R. Accad. 
dei Lincei, Roma (5) 28 (1914), 358; Chem. Zentralbl. 1914, II]. 475. — * Comp. Report April 1905, 18; October © ; 
1918, 148. — 7%) Atti R. Accad. dei Lincei, Roma (5) 28, I. (1914), 347; Chem. Zentraibl. 1914, Il. 481. 
