280 REPORTS ON THE STATE OF SCIENCE. 
obtain, by the action of magnesium methyl iodide, optically active 
A?-p-menthenoal (8) 
CH,.CH 
CH, .CHY Se. ’H,), 
oR ine ye C(OH)(CH,), 
g° 2 
When the latter compound, however, is simply left in contact with an 
ethereal solution of magnesium methyl iodide at the ordinary tempera- 
ture, it is converted into the corresponding optically active unsaturated 
hydrocarbon, A*-*°-y-menthadiene 
CI 
In many cases only unsaturated hydrocarbons can be obtained and 
not the corresponding tertiary alcohols, if it so happens that the latter 
are very unstable. Klages, in particular, prepared a large number of 
unsaturated 1’-alkylated styrenes, of which an example has already been 
quoted, namely, metho-(1’)-vinylbenzene. When this hydrocarbon is 
reduced it is converted into zsopropyl benzene, C;H,.CH(CH;),, with 
great ease. This method in the hands of Klages has proved highly 
useful for making a large number of saturated benzenoid hydrocarbons, 
which are difficult to prepare by other methods. 
Various stilbene derivatives have been studied by F. and L. Sachs,! 
thus : p-dimethylaminobenzaldehyde, (CH;),N.C,H,.CHO, with mag- 
nesium benzyl chloride gives the alcohol 
(CH,).N . C,H, . CH(O1) . CH,C,H, 
and this, on distillation under diminished pressure, forms 4-dimethyl- 
aminostilbene, (CH;),N .C,;H,.CH : CHC,H;. 
The same authors? acted on p-dimethylaminobenzaldehyde with mag- 
nesium methyl iodide and obtained methyl p-dimethylaminopheny]l- 
earbinol, (CH;),N.C,;H,.CH(OH).CH:;, from which, however, water 
was not eliminated in the manner expected. Klages’ method of heating 
the reaction product with an excess of magnesium alkyl halide at 100° 
did not lead to the formation of dimethylaminostyrene, as was anticipated, 
but N-dimethylcumidine was formed thus :— 
(CH,),N . C,H, . CH(OMgBr) . CH, + CH,MgBr = (CH,),N . C,H, . CH(CH,), 
+ MgO + MgBr, 
The formation of hydrocarbons of the acetylene series by aid of the 
Grignard action has been imperfectly studied. According to Oddo ® mag- 
nesium bromoacetylene, CH : CMgBr, is produced when a current of 
dry acetylene is passed into magnesium phenyl bromide, and from this 
derivatives of the acetylene series are obtained. 
(b) Saturated hydrocarbons.—Magnesium organic compounds are 
vigorously acted on by water with the production of hydrocarbons. This 
was one of the first observations which Grignard made with his reagents.* 
1 Ber., 1905, 38, 511. 
2 Thid., 1905, 38, 517. Compare Sachs and Michaelis, ibid., 1906, 39, 2163. 
% Atti R. Accad. Lincei, 1904 [5], 18, 187. 
* Ann. Chim, Phys,, 1901, 24, 438; Tissier and Grignard, Compt. rend., 1901, 
132, 835. 
