Novel Cyclization of Dimeric Dianions of Anils or Aldehydes with Triphosgene 49
1,3-Diheptyl-4,5-bisphenyl-imidazolidin-2-one
4,5-Bis(4-chlorophenyl)-1,3-dioxolan-2-one (4e):
light green crystals, m.p.:122–124◦C, νmax(KBr)/
cm−1: 1797, 1494, 1417, 1345, 821, 799, δH: 6.88–
6.90 (4H, d, J = 8.0 Hz), 7.16–7.18 (4H, d, J = 8.0
Hz), 5.95 (2H, s), m/z(%): 308 (M+, 21.26), 248 (2.23),
89 (100), Anal. C15H10ClO3. Calcd. C, 58.25; H, 3.24.
Found C, 58.20; H, 3.25%.
4,5-Bis(4-nitrophenyl)-1,3-dioxolan-2-one (4f):
light green crystals, m.p.: 162–164◦C, νmax(KBr)/
cm−1: 1745, 1608, 1523, 1388, 1347, 944, 849,
δH: 7.54–7.56 (4H, d, J = 8.0 Hz), 8.23–8.25 (4H,
d, J = 8.0 Hz), 5.28 (2H, s), m/z(%): 330(M+,
2.03), 137 (100), Anal. C15H10N2O3. Calcd. C, 54.55;
H, 3.03; N, 8.48. Found C, 54.50; H, 3.06; N,
8.45%.
(2j): Colorless crystals, m.p.: 106–108◦C, νmax(KBr)/
cm−1: 1715, δH: 6.79–8.04 (10H, m), 6.30 (2H, s),
3.50–3.68 (4H, m), 0.80–1.35 (26H, m), m/z(%): 434
(M+, 1.99), Anal. C29H42N2O. Calcd. C, 80.18; H,
9.67; N, 6.45. Found C, 80.16; H, 9.63; N, 6.47%.
1,3-Dicyclohexyl-4,5-bisphetnyl-imidazolidin-2-
one (2k): Colorless crystals, m.p.: 164–166◦C,
νmax(KBr)/cm−1: 1720, δH: 7.22–7.60 (10H, m), 6.26
(2H, s), 3.44 (2H, m), 0.51–1.85 (20H, m), m/z(%):
402 (M+, 2.09), Anal. C27H34N2O. Calcd. C, 80.59; H,
8.45; N, 6.96. Found C, 80.57; H, 8.43; N, 6.94%.
1,3-Dicyclohexyl-4,5-bis (4-methylphenyl)-imida-
zolidin-2-one (2l): Colorless crystals, m.p.: 174–
176◦C, νmax(KBr)/cm−1: 1720, δH: 6.75–7.12 (8H, m),
6.26 (2H, s), 3.38 (2H, m), 2.19 (6H, s), 0.99–1.83
(20H, m), m/z(%): 430 (M+, 2.09), Anal. C29H38N2O.
Calcd. C, 80.93; H, 8.84; N, 6.51. Found C, 80.9; H,
8.87; N, 6.53%.
REFERENCES
[1] (a) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42,
6573; (b) Molander, G. A. Chem Rev 1992, 92, 29;
(c) Molander, G. A. Organic Reaction 1994, 46, 211;
(d) Molander, G. A.; Harris, C. R. Chem Rev 1996, 96,
307; (e) Krief, A.; Laval, M. A. Chem Rev 1999, 99,
745; (f) Steel, P. G. J Chem Soc, Perkin Trans 1 2001,
2727.
[2] Girard, P.; Namy, J. L.; Kagan, H. B. J Am Chem Soc
1980, 102, 2693.
[3] Curran, D. P.; Chen, M. H.; Kim, D. J Am Chem Soc
1989, 111, 6265; (b) Fukuzawa, S.; Tsuchimoto, T.
Synlett 1993, 803.
[4] Fukuzawa, S.; Nakanishi, A.; Fujinami, T.; Sakai, S.
J Chem Soc, Chem Commun 1986, 624; (b) Ot-
subo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron
Lett 1986, 27, 5763.
[5] Sasaki, M.; Collin, J.; Kagan, H. B. New J Chem 1992,
16, 89; (b) Souppe, J.; Namy, J. L.; Kagan, H. B. Tetra-
hedron Lett 1982, 23, 3497.
4,5-Bisphenyl-1,3-dioxolan-2-one (4a): Colorless
crystals, m.p.: 120–122◦C, νmax(KBr)/cm−1: 1785,
1498, 1450, 774, 748, 696, δH: 6.92–7.32 (10H, m),
5.98 (2H, s), m/z(%): 240 (M+, 17.86), 212 (17.65),
195 (16.45), 178 (9.81), 105 (100), Anal. C15H12O3.
Calcd. C, 75.00; H, 5.00. Found C, 74.90; H, 5.04%.
4,5-Bis(4-methylphenyl)-1,3-dioxolan-2-one (4b):
Colorless crystals, m.p.: 118–121◦C, νmax(KBr)/ cm−1:
1797, 1516, 1456, 1171, 1051, 882, δH: 6.82–6.84 (4H,
d, J = 8.0 Hz), 6.94–6.96 (4H, d, J = 8.0 Hz), 5.91
(2H, s), 2.23 (6H, s), m/z(%): 268 (M+, 39.46), 224
(25.89), 104 (100), Anal. C17H16O3. Calcd. C, 76.12;
H, 5.97. Found C, 76.08; H, 5.90%.
4,5-Bis(4-methoxyphenyl)-1,3-dioxolan-2-one
(4c): Colorless crystals, m.p.:170–171◦C, νmax(KBr)/
cm−1: 1805, 1523, 1507, 1449, 832, 758, δH: 6.90–6.93
(4H, m), 7.45–7.49 (4H, m), 5.92 (2H, s), 3.84 (6H, s),
m/z(%): 298 (M+, 100), 226 (47.16), 211 (67.23), Anal.
C17H16O5. Calcd. C, 68.00; H, 5.33. Found C, 67.86;
H, 5.30%.
[6] Molander, G. A.; Etter, J. B.; Harring, L. S.; Thorel,
P. J. J Am Chem Soc 1991, 113, 8036.
[7] Inanaga, J.; Handa, Y.; Tabuchi, T.; Ostubo, K.;
Yamaguchi, M.; Hanamoto, T. Tetrahedron Lett
1991, 32, 6557; (b) Kamemasa, S.; Yamamoto, H.;
Kobayashi, S. Tetrahedron Lett 1996, 37, 8505;
(c) Zhou, L.-H.; Zhang, Y.-M. Tetrahedron Lett 1997,
38, 8063.
[8] Imamoto, T.; Nishimura, S. Chem Lett 1990,
1141.
[9] Namy, J. L.; Kagan, H. B.; Souppe, J. Tetrahedron Lett
1983, 24, 765.
4,5-Bis(3,4-methylenedioxyphenyl)-1,3-dioxolan-
2-one (4d): Colorless crystals, m.p.:154–156◦C,
νmax(KBr)/cm−1: 1789, 1499, 1450, 1403, 934, 858,
817, 771, δH: 6.43–6.65 (6H, m), 5.90 (4H, s), 5.83
(2H, s), m/z(%): 328 (M+, 54.20), 284 (2.61), 268
(1.86), 134 (100), Anal. C17H12O7. Calcd. C, 62.19; H,
3.66. Found C, 62.10; H, 3.64%.
[10] Hofmann, K. Imidazole and its Derivatives: Part I;
Interscience: New York, 1953; p. 226.