- formation of formic acid. 
From magnesium phenylethyl bromide ‘and chloromethyion« eat o eny 
y ©: CH: CH: CAs: : 
methylenecamphor (phenylpropylidenecamphonr), CH a Cha? CoH | 
B.p. 152 to 154° (0.1 mm.); 208 to 210° (13.5 mm.); d3> 1.0094, [2] pmo + 127.990, m1 03% 
Phenylpropylmethylenecamphor (phendinuiyidence inno x 
C: CH: CH: CH: CH: C,H; 3 : ; Leet ae “ae 
CsAia< rae) , from phenylpropylmagnesium bromide and chloro- ae 
methylenecamphor, boils between 221 and 223° (15. mm.); die 0.9990; [e]po0 + 113. 33°; 
Np 1.593735. 
Je: CH: Cc Hi = 
Cyclohexylmethylenecamphor (hexahydrobenzylidenecamphor), CoH - CO : u of 
from magnesium cyclohexyl bromide and chloromethylenecamphor, crystallizes in beau- 4 
tiful, colourless prisms; m. p. 46 to 48°; [@]p»0 + 128.13° (solution of about 10 per cent. 
in benzene)?‘). 
/C:CH: CioH ay a 
a-Naphthylmethylenecamphor, CoH 6G ‘ “3 is obtained through the action ; 
ry 
of magnesium «@-naphthyl bromide on chloromethylenecamphor. - M.'p. 98 to 99.5°; 
b. p. 253 to 254° (12.5 mm.); [@]p20 + 353,62° (solution of 10 per cent. in benzene). 
Endeavours to prepare a diphenyl derivative of methylenecamphor remained ~ 
unsuccessful, a mixture of diphenyl, benzerythrene and some bodies melting between 5 
183 and 184°, 280 and 281°, and 138 to 143° being obtained. The compound of the = 
last named m.p., which had formed but in a small quantity, is perhaps the diphenyl 
derivative looked for. _ = 
The action of magnesium, which had been activated as much as possible by means — 
of iodine, on chloromethylenecamphor in a mixture of ether and benzene likewise led ~ 
to the two substances, the m. pS. of which lie between 183 to 184° and 280 to 281°. 
The optical rotation of some of the methylenecamphor derivatives is lessened con- ~ 
siderably on reduction. This is no proof, however, that a double linking considerably ~ 
increases the optical activity, for it must be taken into eee that a new asym 4 
7C:CH:R CH. CH a 
carbon atom forms: — Coie en + Hy = CoH es 
Through the action of sodium amalgam on isobutylmethylenecamphor in methyl ve 
~ -/CH-CH2: CHa: CH(CH 
alcoholic solution, isoamylcamphor, Ce bo Die ct ee is formed. It is a 
colour- and odourless oil, b. p. 140° (14 mm.); d> 0.9197;- [a]pn0 + 66.789; np 47015. 
Benzylmethylenecamphor, on being reduced with sodium amalgam, is conver gms 
/ CH: CA: CHa C H 
into phenylethylcamphor, CoH 6 es epg - m. p. 60 to 619; b. p. 201 to 230 2 
(15 mm.); bane -++ 22.82° (solution of 10 per cent. in benzene), 
In the same way, phenylethylmethylenecamphor yields phenylpropyleamph 
/ CH: CHe- CHe- CHe- CoH F 
CHC eG ESS, b. p. 208 to 210° (15 mm.); dae 1.0008; [else +523 " 
(solution of about 10 per cent. in benzene); np 1 02883. 
1) See Report April 1906, 101. 
