1134
SADYKOV et al.
Ethylcyclohexane. Experiment: rt 11.85; 112 [M]
+
dom). We used a JZW Scientific DB-5 capillary col-
umn (60 m 0.25 mm 0.2 m) (the Unted States) in
the linear heating mode and the NBS library of mass
spectra (the United States) containing 75000 mass
spectra.
(25), 84 (7), 83 (100), 82 (47), 69 (7), 67 (13), 57 (1),
56 (10), 55 (77), 42 (8), 41 (33); published data [18]:
+
112 [M] (19), 84 (6), 83 (100), 82 (41), 69 (9), 67
(11), 57 (5), 56 (12), 55 (75), 42 (8), 41 (34).
To perform the reaction of cyclohexane with the
Dimethylcyclohexane. Experiment: rt 9.83; 112
[M] (29), 97 (100), 84 (2), 83 (5), 70 (8), 69 (17), 56
+
system Al CCl , a 50-ml glass reactor was charged
4
under Ar with 0.348 g (13 g-at) of Al and several
crystals of iodine. The mixture was heated on an
alcohol burner until the iodine completely sublimed
and was removed from the reactor. The reactor was
placed on a magnetic stirrer, and 7 ml (65 mmol) of
(15), 55 (63), 43 (6), 41 (19); published data [18]
(1,3-dimethylcyclohexane): 112 [M] (28), 97 (100),
84 (3), 83 (5), 70 (10), 69 (19), 56 (21), 55 (88),
43 (9), 41 (27).
+
Methylethylcyclohexane. Experiment: rt 14.03;
cyclohexane and 2 ml (19 mmol) of CCl were added.
4
+
126 [M] (19), 111 (2), 97 (100), 96 (14), 83 (2), 81
Stirring was continued at room temperature for 2 h.
The reaction was accompanied by HCl evolution.
After reaction completion, two layers formed: a trans-
parent upper layer and a dark brown viscous lower
layer containing aluminum chloride and residual alu-
minum metal. The upper layer was separated and
filtered through Al O . Determination of the bromine
(7), 70 (3), 69 (19), 56 (9), 55 (86), 43 (7), 41 (21);
published data [18] (cis-1-methyl-3-ethylcyclohexane):
+
126 [M] (15), 111 (2), 97 (100), 96 (14), 83 (2), 81
(5), 70 (3), 69 (20), 56 (10), 55 (91), 43 (8), 41 (23).
Trimethylcyclohexane. Experiment: rt 11.75; 126
+
[M] (26), 111 (97), 97 (3), 84 (2), 83 (4), 70 (10), 69
2
3
number showed the absence of unsaturated bonds in
the products. A GLC analysis of the resulting trans-
parent liquid revealed the presence of dimethyldeca-
lins (39%) nd unchanged cyclohexane (19.6%). The
(100), 56 (12), 55 (51), 43 (8), 42 (9), 41 (26); pub-
lished data [18] (cis,cis-1,3-trimethylcyclohexane):
+
126 [M] (23), 111 (95), 97 (2), 84 (2), 83 (4), 70
(10), 69 (100), 56 (12), 55 (56), 43 (10), 42 (5), 41
(30).
+
products giving a group of peaks with [M] 166
(GC/MS) were isolated by preparative chromatog-
13
Tetramethylcyclohexane. Experiment: rt 14.82;
raphy. Their C NMR analysis showed that the sam-
+
140 [M] (2), 125 (100), 97 (1), 84 (7), 83 (40), 70
ples contained 45% E3,E8-dimethyl-trans-bicyclo-
[4.4.0]decane, 41% E3,E9-dimethyl-trans-bicyclo-
[4.4.0]decane, four unidentified isomers of dimethyl-
(12), 69 (99), 57 (14), 56 (9), 55 (33), 43 (12), 41
(26); published data [18] (1,1,3,5-tetramethylcyclo-
hexane): 125 (92), 97 (3), 84 (7), 83 (53), 70 (6), 69
(100), 57 (15), 56 (11), 55 (34), 43 (13), 41 (27).
+
+
decalin with [M] 166 (2 3% each), and five other
isomers with [M] 166 (0.2 0.3% each).
+
13
Decalin. Experiment: rt 21.55; 138 [M] (99), 110
E3,E8-Dimethyl-trans-bicyclo[4.4.0]decane.
C
(9), 108 (18), 96 (71), 95 (60), 82 (71), 81 (61), 69
(41), 68 (87), 67 (100), 55 (34), 41 (51); published
NMR spectrum (CDCl ), , ppm (in parentheses are
3
1
2
6
7
3
published data [16]): C , C , C , C 43.0, (43.0); C ,
+
data [18] (trans-decalin): 138 [M] (100), 110 (7),
8
4
9
5
10
C
33.1 (33.1); C , C 35.6 (35.6); C , C 34.3
109 (17), 96 (58), 95 (63), 82 (60), 81 (54), 69 (45),
68 (91), 67 (91), 55 (41), 41 (82).
3
8
+
(34.2); C CH , C CH 22.8 (22.8); [M] 166.
3
3
13
+
E3,E9-Dimethyl-trans-bicyclo[4.4.0]decane.
C
Trimethyldecalin. Experiment: rt 29.25; 180 [M]
1
2
10
3
9
NMR spectrum: C , C , C 43.3 (43.3); C , C 33.1
(33.1); C , C 35.7 (35.7); C , C 34.0 (34.0); C
42.9 (42.9); C CH , C CH 22.9 (22.8); [M] 166.
(74), 165 (98), 138 (3), 137 (4), 123 (15), 109 (94),
95 (100), 83 (34), 82 (18), 81 (67), 69 (30), 67 (37),
55 (55); published data [18] (3,4,8-trimethyldecalin):
4
8
5
7
6
3
9
+
3
3
+
180 [M] (74), 165 (97), 138 (5), 137 (6), 123 (21),
Mass spectra. Methylcyclopentane. Experiment:
+
109 (94), 95 (100), 83 (40), 82 (21), 81 (70), 69 (30),
67 (39), 55 (68).
rt [retention time (min)] 5.98; m/z (I , %): 84 [M]
rel
(17), 69 (59), 57 (5), 56 (100), 55 (28), 42 (24), 41
(51); published data [18]: 84 [M] (16), 69 (32), 57
+
Dimethyladamantane. Experiment: rt 24.30; 164
+
(5), 56 (100), 55 (26), 42 (28), 41 (64).
[M] (10), 150 (13), 149 (100), 107 (18), 95 (6), 93
+
(31), 91 (9), 81 (7), 79 (9), 77 (7), 67 (6), 55 (6); pub-
Methylcyclohexane. Experiment: rt 8.13; 98 [M]
+
lished data [17] (1,4-dimethyladamantane): 164 [M]
(51), 84 (7), 83 (100), 82 (18), 70 (20), 69 (20), 67
(5), 56 (21), 55 (59), 42 (19), 41 (31); published data
(14), 150 (13), 149 (100), 107 (18), 95 (11), 93 (35),
91 (11), 81 (17), 79 (16), 77 (11), 67 (13), 55 (14).
+
[18]: 98 [M] (41), 84 (7), 83 (100), 82 (17), 70 (20),
69 (21), 67 (4), 56 (28), 55 (83), 42 (30), 41 (46).
Trimethyladamantane. Experiment: rt 24.67; 178
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 77 No. 7 2004