Summary
-
1.
A study has been made of the reactions of methylcyclohexane in the liquid phase in presence of anhydrous aluminum chloride at 80° under normal pressure.
-
2.
It has been established that when methylcyclohexane reacts with aluminum chloride under these conditions it not only isomerizes with shrinkage of the ring into dimethylcyclopentane, but also undergoes the process of methyl-group redistribution to a small extent and, as a result, dimethylcyclohexane and cyclohexane are formed.
-
3.
It has been shown that in the reaction of aluminum chloride with toluene under analogous conditions there is a redistribution of methyl groups resulting in the formation of benzene and a mixture of isomeric xylenes.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
N.D.Zelinsky and I.Pappe. J.Russ.Chem.Soc., 37, 625 (1905); M.B.Turova-Polyak and coworkers. J.Gen.Chem., 9, 233, 429, 1279, (1939); 10, 172, 1435 (1940); N.D.Zolinsky, M.B.Turova-Polyak, and G.R.Gasan-Zade. Proc.Acad.Sci.USSR, 32, 8, 550 (1941); M.B.Turova-Polyak and coworkers. J.GenChem., 11, 817, 824 (1941); 13, 353 (1943); 14, 337 (1944); 16, 825, 829 (1946); 17, 137 (1947); 18, 179 (1948); Proc.Acad.Sci.USSR, 60, 5, 807 (1948).
O.Aschan. Ann., 324, 10 (1902); C.D.Nanitzescu and J.P.Cantuniari. Ber. 66, 7–9, 1097–1100 (1933); V.Grignard and R.Stratford. Comptes rend., 178,2143 (1924).
V.N.Ipatev and V.I.Komarevsky. J.Am.Chem.Soc., 56, 1926 (1934); L.Glasebrook and W.W.C.Lovell. J.Am.Chem.Soc., 61, 1717 (1939); see Yu.A.Arbuzov and N.D. Zelinsky, Proc.Acad.Sci.USSR, 23, 793 (1939).
R.Anschutz and H.Immendorf. Ber., 17, 2816 (1884); 18, 659 (1885); C.Jacobsen. Ber., 18, 338 (1885); R.Heiseu and A.Tchl. Ann., 270 155 (1892); F.Fischer and H.Niggeman. Ber., 49, 1475 (1916); I.F.Norris and G.T.Vaala. J.Am.Chem.Soc., 61, 2131 (1939).
N.I.Shuykin and M.S.Prokhorova. J.Gen.Chem., 16, 835 (1946).
N.D.Zelinsky. Ber., 30, 387 (1897).
G.Chavanne. Bull.soc.chim.Belg., 39, 402 (1930).
F.Ullmann. Ber., 36, 1798 (1903).
B.L.Moldavsky, G.D.Kamusher, and M.V.Kobylskaya. J.Gen.Chem., 7, 167 (1937).