M. Oda et al. / Tetrahedron Letters 43 (2002) 3485–3488
3487
,
Figure 2. Atomic distances (A) in the crystal of the cation 4.
References
Haramoto, K.; Miyatake, R.; Kuroda, S. Synthesis
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14. Shapiro, R. H. Org. React. 1976, 23, 405–507.
15. Selected data for new compounds. 4: mp 217–218°C;
umax (CH3CN)/nm 232, 297sh, 311, 364, 383; lH (400
MHz; CD3CN), 1.32 (4H, dm, 12.4), 1.57 (2H, tt, 12.4,
3.4), 1.65–1.78 (4H, m), 1.90–2.02 (6H, m), 2.21 (4H,
td, 12.4, 3.4), 7.43 (2H, d, 5.6), 8.06 (2H, d, 5.6), 8.79
(2H, s), 8.89 (1H, s); lC (100 MHz; CD3CN), 25.0 (C3,
5, 3%%, 5%%), 26.1 (C4, 4%%), 33.4 (C2, 6, 2%% 6%%), 62.0 (C1,
1%%), 134.3 (C3%, 5%), 137.2 (C3%), 140.4 (C8%, 9%), 160.8
(C2%, 6%), 167.3 (C3%a, 4%a), 173.8 (C7%a, 9%a); wmax (KBr)/
cm−1 2928s, 1731m, 1359m, 1085s, 867w, 764m, 622s;
m/z (rel. int.) 302 (M+, 100), 273 (13), 259 (14), 247
(19), 217 (21), 202 (19), 191 (26), 165 (11), 69 (11); EA
calcd for C23H27ClO4·0.2 CH2Cl2; C, 65.84; H, 6.53,
found C, 65.69; H, 6.73. 7: lH (400 MHz; CDCl3), 1.21
(4H, m), 1.51 (12H, m), 1.74 (4H, m), 2.89 (4H, s),
2.99 (2H, s), 3.19 (6H, s), 6.94 (2H, m), 7.12 (2H, m);
lC (100 MHz; CDCl3), 21.7, 24.7, 25.4, 34.1, 44.7, 48.8,
75.8, 132.1, 133.8, 135.9, 198.0; wmax (liq. film)/cm−1
2933s, 2856s, 1663s, 1455m, 1256m, 1147m, 1073s,
927w, 817w, 742m; m/z (rel. int.) 400 (M+, 8), 368 (23),
336 (17), 240 (32), 149 (32), 113 (100), 81 (64), 69 (26);
HRMS calcd for C25H36O2 400.2613, found 400.2569.
8: Creamy white prisms. Mp >250°C (decomposed);
umax (CH3OH) nm 238, 249, 257sh, 317; lH (400 MHz;
CDCl3), 1.21 (2H, m), 1.30 (8H, m), 1.56 (4H, m), 1.75
(6H, m), 2.34 (4H, s), 3.00 (2H, s), 6.96 (2H, m); lC
(100 MHz; CDCl3) 16.1, 23.5, 25.3, 35.8, 44.3, 46.8,
131.1, 135.6, 170.7, 205.2; wmax (KBr)/cm−1 2935m,
1691s, 1556w, 1264w, 1195m, 1092w, 919w, 754w; m/z
(rel. int.) 336 (M+, 100), 293 (5), 279 (7), 141 (7), 115
(6), 81 (5); EA of the bis(2,4-dinitrophenylhydrazone)
derivative (mp >300°C), calcd for C35H36N8O8; C,
60.34; H, 5.21; N, 16.08, found C, 60.05; H, 5.28; N,
15.78. 9: lH (400 MHz; CDCl3), 1.14 (2H, m), 1.50
(8H, m), 1.56 (4H, m), 1.75 (6H, m), 3.19 (2H, s), 6.21
(2H, d, 5.4), 6.35 (2H, s), 6.89 (2H, d, 5.4); lC (100
MHz; CDCl3), 25.9 (C3, 5, 3%%, 5%%), 26.7 (C4, 4%%), 29.3
(C4%), 33.3 (C2, 6, 2%%, 6%%), 58.0 (C1, 1%%), 123.2 (C2%, 6%),
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