ORDER
REPRINTS
2,3-DIALKYLQUINONES
3881
186.4. Anal. Calcd for C16H22N2O6: C, 56.80; H, 6.55; N, 8.28. Found: C,
56.76; H, 6.56; N, 8.23.
2,3-Bis(2-nitrocyclohex-2-ylmethyl)-5,6-dimethyl-1,4-benzoquinone (5c).
Yellow solid, mp 194ꢁC (ethanol). H NMR (CDCl3): d 1.21 (m, 4H), 1.55
1
(m, 12H), 2.02 (s, 6H), 2.33 (m, 4H), 2.96 (s, 4H). 13C NMR (CDCl3): d 12.6,
22.2, 24.2, 34.8, 36.5, 91.8, 141.2, 142.1, 186.1. Anal. Calcd for C22H30N2O6:
C, 63.14; H, 7.23; N, 6.69. Found: C, 63.11; H, 7.28; N, 6.74.
2,3-Bis(2-nitrocyclohept-2-ylmethyl)-5,6-dimethyl-1,4-benzoquinone
(5d). Yellow solid, mp 111ꢁC (ethanol). 1H NMR (CDCl3): d 1.55 (m, 16H),
1.84 (m, 4H), 2.05 (s, 6H), 2.33 (m, 4H), 3.05 (s, 4H). 13C NMR (CDCl3): d
12.6, 22.7, 29.4, 36.5, 37.1, 95.3, 141.2, 142.1, 186.4. Anal. Calcd for
C24H34N2O6: C, 64.55; H, 7.67; N, 6.27. Found: C, 64.61; H, 7.66; N, 6.24.
2,3-Bis(2,2-dimethyl-5-nitro-1,3-dioxan-5-ylmethyl)-5,6-dimethyl-1,4-
benzoquinone (5f ). Brown solid, mp 225ꢁC (ethanol). H NMR (CDCl3): d
1
1.36 (s, 6H), 1.50 (s, 6H), 2.02 (s, 6H), 3.10 (s, 4H), 4.01 (d, J ¼ 12.9 Hz, 4H),
4.27 (d, J ¼ 12.9 Hz, 4H). 13C NMR (CDCl3): d 12.6, 22, 24.4, 29.5, 63.9,
84.3, 99, 141.4, 143.1, 186.9. Anal. Calcd for C22H30N2O10: C, 54.77; H,
6.27; N, 5.81. Found: C, 54.75; H, 6.32; N, 5.77.
2,3-Bis(2-methyl-2-nitropropyl)-1,4-naphthoquinone (6a). Yellow solid,
mp 151ꢁC (ethanol). H NMR (CDCl3): d 1.51 (s, 12H), 3.24 (s, 4H), 7.68
1
(m, 2H), 8.01 (m, 2H). 13C NMR (CDCl3): d 26.5, 36.6, 87.9, 126.8, 131.5,
134.2, 144.9, 184.1. Anal. Calcd for C18H20N2O6: C, 59.99; H, 5.59; N, 7.77.
Found: C, 59.98; H, 5.51; N, 7.68.
2,3-Bis(2-methyl-2-nitropentyl)-1,4-naphthoquinone (6b). Yellow solid,
mp 116ꢁC (ethanol). H NMR (CDCl3): d 0.93 (t, J ¼ 7 Hz, 6H), 1.16–1.45
1
(m, 4H), 1.46 (s, 6H), 1.77 (m, 2H), 2.08 (m, 2H), 3.22 (d, J ¼ 14.3 Hz, 2H),
3.34 (d, J ¼ 14.3 Hz, 2H), 7.74 (m, 2H), 8.08 (m, 2H). 13C NMR (CDCl3):
d 13.9, 17.4, 21.8, 36, 42.3, 91.3, 126.8, 131.6, 134.1, 145, 184.2. Anal. Calcd
for C22H28N2O6: C, 63.45; H, 6.78; N, 6.73. Found: C, 63.40; H, 6.79;
N, 6.66.
2,3-Bis(2-nitrocyclohex-2-ylmethyl)-1,4-naphthoquinone (6c). Yellow
solid, mp 192ꢁC (ethanol). H NMR (CDCl3): d 1.20 (m, 4H), 1.63 (m,
1
12H), 2.38 (m, 4H), 3.13 (s, 4H), 7.74 (m, 2H), 8.08 (m, 2H). 13C NMR
(CDCl3): d 22.2, 24.2, 34.8, 36.7, 91.7, 126.8, 131.5, 134, 144.7, 183.8.
Anal. Calcd for C24H28N2O6: C, 65.44; H, 6.41; N, 6.36. Found: C, 65.45;
H, 6.35; N, 6.33.
2,3-Bis(2-nitrocyclohept-2-ylmethyl)-1,4-naphthoquinone (6d). Yellow
solid, mp 132ꢁC (ethanol). H NMR (CDCl3): d 1.55 (m, 16H), 1.89 (m,
1
4H), 2.36 (m, 4H), 3.21 (s, 4H), 7.75 (m, 2H), 8.07 (m, 2H). 13C NMR
(CDCl3): d 22.7, 29.4, 36.7, 37.1, 95.5, 126.8, 131.6, 134, 144.9, 184.1.
Anal. Calcd for C26H32N2O6: C, 66.65; H, 6.88; N, 5.98. Found: C, 66.60;
H, 6.89; N, 5.94.