320 Herna´ndez-D´ıaz, Flores-Parra, and Contreras
[21] Klaebe, A.; Brazier, J. F.; Cachapuz Carrelhas, A.;
Garrigues, B.; Marre, M. R.; Contreras, R. Tetrahe-
dron 1982, 38, 2111.
3,4-Benzimidazole-5,6-benzo-2-phenyl-2-seleno-
1,3,2-oxazaphosphorinane (31)
[22] PC Spartan Plus 1.5, Wavefunction Inc., Irvine C. A.,
1996–1998.
[23] Mun˜oz, A.; Gallagher, M.; Klaebe, A.; Wolf, R.
Tetrahedron Lett 1976, 673.
[24] Shevchenco, I. V.; Fischer, A.; Jones, P. G.; Schmut-
zler, R. Chem Ber 1992, 125, 1325.
[25] Kemp, G.; Trippett, S. J Chem Soc, Perkin Trans 1
1979, 879.
[26] Meyer, T. G.; Fischer, A.; Jones, P. G.; Schmutzler, R.
Z Naturforsch 1993, 48B, 659.
[27] Criegern, T.; Schmidpeter, A. Z Naturforsch 1979,
34B, 762.
From 300 mg (0.95 mmol) of 7 and 90 mg (1.14
mmol) of selenium refluxed for 1 h, a yellow
solid was obtained in quantitative yield (363 mg).
Mp 176–178◦C. MS: m/z (%): 396.00 (58) [M]+,
394.00 (29), 332.15 (97), 316.15 (29), 272.10 (22),
269.20 (22), 239.15 (62), 210.20 (100), 182.25 (42).
IR (KBr): ν (cm−1) 2919, 2849, 1624, 1560, 1478,
1187, 1137, 1034, 748, 696, 543. Anal. calcd.
(C19H13N2OPSe ·CH3COCH3) [453.33]: C, 58.28; H,
4.22; N, 6.17. Found: C, 57.97; H, 4.45; N, 6.53.
[28] Cong, C. B.; Gence, G.; Garrigues, B.; Koenig, M.;
Mun˜oz, A. Tetrahedron 1979, 35, 1825.
[29] Kukhar, V. P.; Grichkun, E. V.; Rudavskii, V. P. Zh
Obshch Khim 1980, 50, 1017.
[30] Chaus, M. P.; Gusar, N. I.; Gololobov, Y. G. Zh Obshch
Khim 1982, 52, 24.
[31] Bertrand, G.; Majoral, J.-P.; Baceiredo, A. Tetrahe-
dron Lett 1980, 21, 5015.
REFERENCES
[1] Ceniceros-Go´mez, A. E.; Ramos-Organillo, A.;
Herna´ndez-D´ıaz, J.; Nieto-Mart´ınez, J.; Contreras,
R.; Castillo-Blum, S. E. Heteroat Chem 2000, 11, 392.
¨
[2] Tavman, A.; Ulku¨seven, B. Main Group Met Chem
2001, 24, 205.
[32] Herna´ndez-D´ıaz, J. PhD thesis. Chemistry Depart-
ment, Cinvestav, Mexico, 2002.
[33] Lowther, N.; Beer, P. D.; Hall, C. D. Phosphorus and
Sulfur 1988, 35, 133.
[3] Tlahuextl, M.; Mart´ınez-Mart´ınez, F. J.; Rosales-Hoz,
M. J.; Contreras, R. Phosphorus, Sulfur, and Silicon
1997, 123, 5.
[4] (a) Herna´ndez-D´ıaz, J.; Contreras, R.; Wrackmeyer,
B. Heteroat Chem 2000, 11, 11; (b) Herna´ndez-D´ıaz,
J.; Flores-Parra A.; Contreras, R. Heteroat Chem
2004, 15(4), 321.
[5] Fischer, A.; Neda, I.; Jones, P. G.; Schmutzler, R.
Phosphorus, Sulfur, and Silicon 1993, 83, 135.
[6] Kuliev, A. K.; Moskva, V. V.; Akhmedzade, D. A.;
Sakhnovskaya, E. B.; Zykova, T. V. Zh Obshch Khim
1984, 54, 1671.
[7] Tebby, J. C. (Ed.). CRC Handbook of Phosphorus-31
NMR Data; CRC Press: Boca Raton, FL, 1991.
[8] Gloede, J.; Pieper, U.; Habicher, W. D.; Schneider, M.
Z Anorg Allg Chem 2002, 628, 480.
[9] Goodridge, R. J.; Hambley, T. W.; Ridley, D. D. Aust
J Chem 1986, 39, 591.
[34] (a) Kojima, S.; Sugino, M.; Matsukawa, S.;
Nakamoto, M.; Akiba, K. J Am Chem Soc 2002,
124, 7674; (b) Kajiyama, K.; Yoshimune, M.;
Nakamoto, M.; Matsukawa, S.; Kojima, S.; Akiba, K.
Org Lett 2001, 3, 1873.
[35] Muthiah, C.; Said, M. A.; Pu¨lm, M.; Herbst-Irmer, R.;
Swamy, K. C. K. Polyhedron 2000, 19, 63.
[36] Fischer, A.; Neda, I.; Kaukorat, T.; Sonnenburg, R.;
Jones, P. G.; Schmutzler, R. Z Natursforsch 1994,
49B, 939.
[37] Emsley, J.; Hall, D. The Chemistry of Phosphorus;
Harper and Row Publishers; New York, 1976.
[38] Bakhmutova, E. V.; No¨th, H.; Contreras, R.;
Wrackmeyer, B. Z Anorg Alg Chem 2001, 627, 1846.
[39] Raju, C. N.; Naidu, M. S. R.; John, E. O.; Reddy, M.
C. Magn Reson Chem 1990, 28, 908.
[10] Nakanishi, K. (Ed.). One-Dimensional and Two-
Dimensional NMR Spectra by Modern Pulse
Techniques; Kodansha: Tokyo, 1990.
[40] Mikolajczyk, M.; Omelanczuc, J.; Abdukakharov, W.
S. Tetrahedron 1982, 38, 2183.
[11] Padilla-Mart´ınez, I. I.; Andrade-Lo´pez, N.; Gama-
Goicoechea, M.; Aguilar-Cruz, E.; Cruz, A.; Contreras,
R.; Tlahuext, H. Heteroat Chem 1996, 7, 323.
[12] Padilla-Mart´ınez, I. I.; Ariza-Castolo, A.; Contreras,
R. Magn Reson Chem 1993, 31, 189.
[13] Mart´ınez-Mart´ınez, F. J.; Leo´n Romo, J. L.; Padilla-
Mart´ınez, I. I.; Rosales-Hoz, M. J.; Contreras, R.
Phosphorus, Sulfur, and Silicon 1996, 115, 217.
[14] Garrigues, B.; Mun˜oz, A.; Koenig, M.; Sa´nchez, M.;
Wolf, R. Tetrahedron 1977, 33, 635.
[41] Stec, W. J.; Okruszeck, A.; Michalski, J. J Org Chem
1976, 41, 233.
[42] El-Barbary, A. A.; Lawesson, S. O. Tetrahedron 1981,
37, 2641.
[43] (a) Allen, D. W.; Taylor, B. F. J Chem Soc, Dalton
Trans 1982, 51; (b) Andersen, N. G.; Keay, B. A. Chem
Rev 2001, 101, 997.
´
[44] (a) Enikeev, K. M.; Vayandina, E. V.; Ismaev, I. E.;
Buina, N. A.; Il’Yasov, A. V.; Nuretdinov, I. A. Zh
Obsch Khim 1983, 53, 2143 (Chem Abstr 1984, 100,
22721); (b) Duddeck, H. Prog Nucl Magn Reson
Spectros 1995, 27, 1.
[15] Mun˜oz, A.; Koenig, M.; Garrigues, B.; Wolf, R. Compt
Rend Acad Sci 1972, 274C, 1413.
[16] Mun˜oz, A.; Garrigues, B.; Wolf, R. Phosphorus and
Sulfur 1978, 4, 47.
[17] Sa´nchez, M.; Brazier, J. F.; Houalla, D.; Mun˜oz, A.;
Wolf, R. J Chem Soc, Chem Commun 1976, 730.
[18] Bone, S. A.; Trippett, S.; Whittle, P. J. J Chem Soc,
Perkin Trans I 1977, 80.
[45] Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purifi-
cation of Laboratory Chemicals, 3th ed.; Pergamon
Press, Oxford, 1988.
[46] (a) Hein, D. W.; Alheim, R. J.; Leavitt, J. J. J Am
Chem Soc 1957, 79, 427; (b) Addison, A. W.; Burke,
P. J. J Heterocycl Chem 1981, 18, 803.
[19] Holmes, R. R. J Am Chem Soc 1978, 100, 433.
[20] Wasada, H.; Hirao, K. J Am Chem Soc 1992, 114, 16.
[47] Sheldrick, G. M. SHELXL-97; University of
Go¨ttingen, Go¨ttingen, Germany, 1997.