A new chemical synthesis pathway to obtain tert-butyl-dibromophosphane is proposed and compared to former ones. A first IR and NMR spectroscopic characterization of the molecule is given. IR spectra were recorded between 80 and 660 cm⁻¹ at the SOLEIL Synchrotron facility and between 800 and 3100 cm⁻¹ at the Kassel laboratories. All 42 vibrational modes were calculated using the Gaussian program package. The main abundant isotopologue ^tBuP⁷⁹Br⁸¹Br is chiral, and the barrier to enantiomeric inversion has been determined. Assignments of the observed infrared bands are proposed.

References

1K. B. Dillon, F. Mathey, J. F. Nixon, Phosphorus: The Carbon Copy: From Organophosphorus to Phospha-Organic Chemistry, Wiley Chichester, England 1998.
Google Scholar
2R. J. Gillespie, I. Hargittai, The VSEPR Model of Molecular Geometry, Allyn at Bacon, Boston 1991.
Google Scholar
3A. Rauk, L. C. Allen, K. Mislow, Angew. Chem. 1970, 82, 453.
10.1002/ange.19700821202
Google Scholar
4S. Humbel, C. Bertrand, C. Darcel, C. Bauduin, S. Jugé, Inorg. Chem. 2003, 42, 420.
10.1021/ic026128u
CAS PubMed Web of Science® Google Scholar
5C. C. J. Levin, J. Am. Chem. Soc. 1975, 97, 5649.
10.1021/ja00853a001
CAS Web of Science® Google Scholar
6H. A. Bent, Chem. Rev. 1961, 61, 275.
10.1021/cr60211a005
CAS Web of Science® Google Scholar
7P. W. Davis, R. A. Oetjen, J. Mol. Spectrosc. 1958, 2, 253.
10.1016/0022-2852(58)90078-X
CAS Web of Science® Google Scholar
8R. J. H. Clark, D. M. Rippon, J. Mol. Spectrosc. 1974, 52, 58.
10.1016/0022-2852(74)90005-8
CAS Web of Science® Google Scholar
9M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revision d.01, Gaussian Inc., Wallingford CT 2009.
Google Scholar
10M. Kitamura, M. Tokunaga, T. Ohkuma, R. Noyori, Tetrahedron Lett. 1991, 32, 4163.
10.1016/S0040-4039(00)79892-3
CAS Web of Science® Google Scholar
11V. S. Chan, M. Chiu, R. G. Bergmann, F. D. Toste, J. Am. Chem. Soc. 2009, 131, 6021.
10.1021/ja9014887
CAS PubMed Web of Science® Google Scholar
12O. J. Scherer, W. Gick, Chem. Ber. 1970, 103, 71.
10.1002/cber.19701030112
CAS Web of Science® Google Scholar
13S. Jugé, M. Stephan, J. A. Laffitte, J. P. Genet, Tetrahedron Lett. 1990, 31, 6357.
10.1016/S0040-4039(00)97063-1
CAS Web of Science® Google Scholar
14K. Nikitin, K. V. Rajendran, H. Mueller-Bunz, D. G. Gilheany, Angew. Chem. Int. Ed. 2014, 53, 1906.
10.1002/anie.201309556
CAS PubMed Web of Science® Google Scholar
15M. Baudler, J. Hellmann, Z. Anorg, Allg. Chem. 1981, 480, 129.
10.1002/zaac.19814800916
CAS Web of Science® Google Scholar
16A. Hinke, W. Kuchen, Phosphorus and Sulfur and the Related Elements 1983, 15, 93.
10.1080/03086648308073282
CAS Web of Science® Google Scholar
17A.-M. Hinke, A. Hinke, W. Kuchen, Z. Naturforsch. B Chem. Sci. 1988, 43, 280.
10.1515/znb-1988-0308
CAS Web of Science® Google Scholar
18P. Roy, M. Rouzieres, Z. Qi, O. Chubar, Infrared Phys. Technol. 2006, 49, 139.
10.1016/j.infrared.2006.01.015
CAS Web of Science® Google Scholar
19A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
10.1063/1.464913
CAS Web of Science® Google Scholar
20C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
10.1103/PhysRevB.37.785
CAS PubMed Web of Science® Google Scholar
21S. Grimme, J. Chem. Phys. 2006, 124, 034108/1.
10.1063/1.2148954
CAS Web of Science® Google Scholar

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Tert-butyl-dibromophosphane ^tBuPBr₂—a new chemical synthesis and first spectroscopic characterization