MUKHAMETYANOVA et al.
1194
Methyl tetracosa-2,3-dienoate (2d). Yield 2.06 g
141.62, 141.87, 141.93, 142.14, 142.19, 142.40 (=CH),
142.71, 143.08, 144.39, 144.47, 144.86, 144.97,
145.10, 145.18, 145.30, 145.34, 145.42, 145.35,
145.96, 146.07, 146.15, 146.26, 146.38, 148.18,
148.35, 157.37, 166.21 (C=O). Found, %: C 93.56;
H 3.23. C78H32O2. Calculated, %: C 93.58; H 3.22.
M 1001.0875.
(87%), white crystalline solid. IR spectrum, ν, cm–1:
1962 (C=C=C), 1722 (C=O). 1H NMR spectrum
(CDCl3), δ, ppm: 0.87–0.90 m (3H, CH3), 1.25 s (18H,
CH2), 1.34–1.38 m (2H, 2-H), 1.43–1.46 m (16H,
CH2), 2.12 m (2H, 20-H), 3.72 s (3H, OCH3), 5.57–
5.61 m (2H, CH=). 13C NMR spectrum (CDCl3), δC,
ppm: 14.05 (CH3), 22.64 (C2), 27.43 (C16, C17, C18,
C19, C20), 28.65 (C13), 28.91 (C15), 29.31 (C14), 29.55
(C4), 29.59 (C5), 29.65 (C6, C7, C8, C9, C10, C11, C12),
31.88 (C3), 51.83 (OCH3), 87.82 (=CH), 95.38 (=CH),
166.64 (C=O), 212.33 (=S=). Found, %: C 79.32; H
12.27. C25H46O2. Calculated, %: C 79.30; H 12.25. M
378.6315.
Methyl 5′-hexadecyl-5′H-cyclopenta[1′,2′:1,9]-
(C60-Ih)[5,6]fullerene-3′-carboxylate (3c). Yield
1
75 mg (52%). H NMR spectrum (CDCl3), δ, ppm:
0.87 t (3H, CH3), 1.25 s (8H, CH2), 1.39–1.41 m (2H,
2-H), 1.41 m (2H, 13-H), 1.42–1.44 m (14H, CH2),
1.92–1.96 m (2H, 15-H), 3.93 s (3H, OCH3), 4.71–
4.75 m (1H, CH), 7.86–7.90 m (1H, =CH). 13C NMR
spectrum (CDCl3), δC, ppm: 14.20 (CH3), 22.74 (C2),
28.63 (C13), 28.94 (C15), 29.34 (C14), 29.41 (C4), 29.58
(C5), 29.71 (C6, C8, C9), 29.77 (C10), 29.95 (C11, C12),
31.96 (C3), 52.20 (CH), 57.88 (OSH3), 74.42, 128.59,
129.65, 131.77, 131.93, 132.00, 132.01, 132.06,
132.14, 132.76, 134.00, 135.27, 135.74, 135.97,
139.19, 139.33, 139.69, 140.21, 141.55, 141.61,
141.89, 141.92, 141.98, 142.14, 142.18, 142.23, 142.40
(=CH), 142.63, 142.69, 143.05, 143.10, 144.40,
144.44, 144.88, 144.97, 145.07, 145.16, 145.29,
145.33, 145.44, 145.56, 145.94, 146.07, 146.17,
146.25, 146.35, 147.22, 147.32, 148.15, 148.28,
148.36, 157.17, 164.21 (C=O). Found, %: C 93.28;
H 3.65. C81H38O2. Calculated, %: C 93.26; H 3.67.
M 1043.1672.
Cyclopentafullerenes 3a–3d (general procedure).
A solution of C60 (0.1 g, 0.14 mmol) in 35 mL of
toluene was kept for 12 h, a solution of 0.14 mmol of
ester 2a–2d and 0.14 mmol of triphenylphosphine in
5 mL of toluene was added, and the mixture was
refluxed for 12 h. Compounds 3a–3d were isolated by
column chromatography using toluene and petroleum
ether–ethyl acetate (4:1) as eluents.
Methyl 5′-decyl-5′H-cyclopenta[1′,2′:1,9]-
(C60-Ih)[5,6]fullerene-3′-carboxylate (3a). Yield
1
40 mg (30%). H NMR spectrum (CDCl3), δ, ppm:
0.86 t (3H, CH3), 1.14–1.39 m (14H, CH2), 1.46 m
(2H, 9-H), 2.12 m (2H, 10-H), 3.94 s (3H, OCH3),
4.71–4.74 m (1H, CH), 7.87–7.90 m (1H, =CH).
13C NMR spectrum (CDCl3), δC, ppm: 14.16 (CH3),
22.71 (C2), 28.57 (C9), 29.37 (C8), 29.58 (C5), 29.64
(C7), 29.70 (C6), 29.88 (C4), 31.92 (C3), 35.74 (C11),
52.16 (OCH3), 57.87 (CH), 74.44, 77.28, 132.96,
133.65, 133.98, 135.34, 135.70, 135.97, 140.21, 141.57,
141.93, 142.19, 142.41 (=CH), 142.60, 142.72, 143.11,
144.46, 144.87, 144.98, 145.17, 145.96, 146.19,
146.27, 147.25, 147.34, 148.15, 148.31, 157.19, 164.26
(C=O). Found, %: C 93.90; H 3.32. C75H26O2. Cal-
culated, %: C 93.93; H 2.73. M 959.0077.
Methyl 5′-icosyl-5′H-cyclopenta[1′,2′:1,9]-
(C60-Ih)[5,6]fullerene-3′-carboxylate (3d). Yield
1
55 mg (36%). H NMR spectrum (CDCl3), δ, ppm:
0.91 t (3H, CH3), 1.28 s (18H, CH2), 1.39–1.41 m (2H,
2-H), 1.43–1.55 m (16H, CH2), 2.37–2.40 m (2H, 20-
H), 3.95 s (3H, OCH3), 4.71–4.74 m (1H, CH), 7.72–
7.74 m (1H, =CH). 13C NMR spectrum (CDCl3), δC,
ppm: 14.14 (CH3), 22.70 (C2), 28.59 (C19), 29.37 (C4,
C17, C18), 29.67 (C5, C16), 29.73 (C6, C8–C15), 29.90
(C7), 31.93 (C3), 35.73 (C20), 52.12 (OCH3), 57.87
(CH), 128.20, 128.45, 128.50, 128.55, 128.72, 131.97,
132.06, 132.14, 133.64, 133.79, 133.99, 135.34,
135.72, 135.97, 137.01, 137.09, 139.19, 139.32,
139.68, 140.21, 141.55, 141.61, 141.88, 141.91,
141.97,142.13, 142.18, 142.23, 142.40 (=CH),
142.63,142.69, 143.05, 143.10, 144.39, 144.45, 144.49,
144.86, 144.97, 145.07, 145.16, 145.29, 145.34,
145.44, 145.55, 145.91, 145.94, 146.07, 146.17,
146.25, 146.32, 146.34, 147.22, 147.32, 148.15,
148.15, 150.81, 151.08, 153.03, 157.17, 164.17 (C=O).
Found, %: C 92.89; H 4.21. C85H46O2. Calculated, %:
C 92.87; H 4.22. M 1099.2735.
Methyl 5′-dodecyl-5′H-cyclopenta[1′,2′:1,9]-
(C60-Ih)[5,6]fullerene-3′-carboxylate (3b). Yield
1
57 mg (41%). H NMR spectrum (CDCl3), δ, ppm:
0.86 t (3H, CH3), 1.14–1.39 m (14H, CH2), 1.46–
1.49 m (2H, 9-H), 2.12–2.14 m (2H, 10-H), 3.94 s (3H,
OCH3), 4.71 m (1H, CH), 7.87 m (1H, =CH).
13C NMR spectrum (CDCl3), δC, ppm: 14.17 (CH3),
22.72 (C2), 28.63 (C13), 28.94 (C15), 29.34 (C14), 29.41
(C4), 29.58 (C5), 29.71 (C6, C8, C9), 29.77 (C10), 29.95
(C11, C12), 31.96 (C3), 52.20 (CH), 57.88 (OCH3),
74.42, 128.59, 129.65, 131.77, 131.93, 132.00, 132.01,
132.06, 132.14, 132.76, 134.00, 135.27, 135.74,
135.97, 139.19, 139.33, 139.69, 140.22, 141.54,
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 7 2020