BUTOV et al.
1044
Diethyl ether was distilled off, and the mixture was
heated for 1 h at 110°C. It was then cooled to 20°C,
20 mL of n-hexane was added, and the white precipitate
of 1,1′-biadamantane (4) was filtered off. n-Hexane
and excess toluene were distilled off from the filtrate,
and the product was isolated from the residue by
fractional distillation under reduced pressure. Yield
3.5 g (0.0154 mol, 53%), bp 164°C (3 mm Hg),
mp 42–43°C [19, 20]. Mass spectrum, m/z (Irel, %): 226
(7) [M]+, 135 (100) [Ad]+, 107 (8) [C8H11]+, 91 (18)
[C7H7]+, 79 (15) [C6H7]+, 41 (8) [C3H5]+. Found, %:
C 90.25; H 9.71. C17H22. Calculated: %: C 90.20;
H 9.80. M 226.2.
240 (58) [M]+, 136 (47) 135 (100) [Ad]+, 107 (31)
[C8H11]+, 105 (57) [C8H9], 93 (62) [C7H9]+, 91 (38)
[C7H7]+, 79 (69) [C6H7]+, 77 (61) [C6H5]+, 67 (31)
[C5H6]+, 41 (33) [C3H5]+. Found, %: C 89.99; H 10.01.
C18H24. Calculated, %: C 89.94; H 10.06. M 240.2.
1-(Adamantan-1-ylmethyl)-3,5-dimethylbenzene
(3f) was synthesized in a similar way from 14.3 g
(0.12 mol) of mesitylene (2f) and 4.0 g (0.03 mol) of 1.
Yield 4.7 g (0.0186 mol, 62%), mp 71–73°C, bp 165–
1
166°C (1 mm Hg). H NMR spectrum, δ, ppm: 1.45–
1.82 m (15H, Ad), 2.18–2.27 m (8H, CH3, CH2), 6.10–
6.23 m (3H, C6H3). Found, %: C 89.78; H 10.22.
C19H26. Calculated, %: C 89.70; H 10.30. M 254.2.
2-(Adamantan-1-yl)-2-phenylpropane (3b) was
synthesized in a similar way from 14.4 g (0.12 mol) of
cumene (2b) and 4 g (0.03 mol) of 1. Yield 4.6 g
(0.0183 mol, 61%), mp 61°C, bp 150–152° (1 mm Hg).
1H NMR spectrum, δ, ppm: 1.10 s (6H, CH3), 1.61–
2.21 m (15H, Ad), 7.15–7.81 m (5H, Ph). Mass spec-
trum, m/z (Irel, %): 254 (30) [M]+, 135 (100) [Ad]+, 119
(80) [C6H5C(CH3)2]+, 107 (36) [C8H11]+, 93 (52)
[C7H9]+, 91 (20) [C7H7]+, 79 (52) [C6H7]+, 77 (43)
[C6H5]+. Found, %: C 89.62; H 10.37. C19H26. Cal-
culated, %: C 89.70; H 10.30. M 254.2.
1-(Adamantan-1-ylmethyl)-2,4,5-trimethylben-
zene (3g) was synthesized in a similar way from
16.10 g (0.12 mol) of 1,2,4,5-tetramethylbenzene (2g)
and 4.0 g (0.03 mol) of 1. Yield 6.2 g (0.023 mol,
77%), mp 69–71°C, bp 171–173°C (1 mm Hg).
1H NMR spectrum, δ, ppm: 1.51–1.91 m (15H, Ad),
2.16 d (9H, CH3), 2.31 s (2H, CH2), 6.62 d (2H, C6H2).
Found, %: C 89.54; H 10.46. C20H28. Calculated, %:
C 89.49; H 10.51. M 268.2.
CONFLICT OF INTEREST
The authors declare no conflict of interest.
REFERENCES
1-(Adamantan-1-ylmethyl)-2-methylbenzene (3c)
was synthesized in a similar way from 12.8 g
(0.12 mol) of o-xylene (2c) and 4 g (0.03 mol) of 1.
Yield 4.2 g (0.0174 mol, 58%), nD20 = 1.5612, bp 148–
1
149°C (1 mm Hg). H NMR spectrum, δ, ppm: 1.53–
1. Mokhov, V.M., Saad, K.R, Parshin, G.Yu., and
Butov, G.M., Russ. J. Org. Chem., 2019, vol. 55, p. 640.
2. Lednicer, D., Heyd, W.E., Emmert, D.E., TenBrink, R.E.,
Schurr, P.E., and Day, Ch.E., J. Med. Chem., 1979,
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3. Margosian, D., Speier, J., and Kovacic, P., J. Org. Chem.,
1981, vol. 46, p. 1346.
1.92 m (15H, Ad), 2.39 s (3H, CH3), 2.40 s (2H, CH2),
7.05–7.24 m (4H, C6H4). Found, %: C 90.90; H 10.08.
C18H24. Calculated, %: C 89.94; H 10.06. M 240.2.
1-(Adamantan-1-ylmethyl)-3-methylbenzene
(3d) was synthesized in a similar way from 12.8 g
(0.12 mol) of m-xylene (2d) and 4 g (0.03 mol) of 1.
Yield 4.9 g (0.0204 mol, 68%), nD20 = 1.5529, bp 145–
1
147°C (1 mm Hg). H NMR spectrum, δ, ppm: 1.63–
2.12 m (15H, Ad), 2.47–2.55 m (5H, CH2, CH3), 7.07–
7.31 m (4H, C6H4). Mass spectrum, m/z (Irel, %): 240
(28) [M]+, 135 (100) [Ad]+, 107 (48) [C8H11]+, 105
(54) [MeC6H4CH2], 93 (74) [C7H9], 91 (50) [C7H7]+,
79 (77) [C6H7]+, 77 (54) [C6H5]+, 67 (64) [C5H7]+, 41
(77) [C3H5]+. Found, %: C 89.86; H 10.13. C18H24.
Calculated: %: C 89.94; H 10.06. M 240.2.
4. Kogay, B.E. and Sokolenko, W.A., Tetrahedron Lett.,
1983, vol. 24, p. 613.
5. Butov, G.M., Kamneva, E.A., and Saad, K.R., Russ. J.
Appl. Chem., 2011, vol. 84, p. 730.
6. No, B.I., Butov, G.M., Mokhov, V.M., and Parshin, G.Yu.,
Russ. J. Org. Chem., 2003, vol. 39, p. 1668.
7. No, B.I., Butov, G.M., Mokhov, V.M., and Parshin, G.Yu.,
Russ. J. Org. Chem., 2002, vol. 38, p. 295.
1-(Adamantan-1-ylmethyl)-4-methylbenzene (3e)
was synthesized in a similar way from 12.8 g
(0.12 mol) of m-xylene (2d) and 4 g (0.03 mol) of 1.
Yield 4.7 g (0.0196 mol, 65%), mp 39–40.5°C,
bp 143–145°C (1 mm Hg). 1H NMR spectrum, δ, ppm:
1.55–2.02 m (15H, Ad), 2.35–2.43 m (5H, CH2, CH3),
7.01–7.22 m (4H, C6H4). Mass spectrum, m/z (Irel, %):
8. Butov, G.M., Mokhov, V.M., Kamneva, E.A., and
Saad, K.R., Russ. J. Org. Chem., 2009, vol. 45, p. 1721.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 6 2020