1,3,6-Azadiphosphacycloheptanes: A novel type of heterocyclic diphosphines
Corresponding Author
Andrey A. Karasik
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian FederationSearch for more papers by this authorAnna S. Balueva
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorElvira I. Moussina
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorRoman N. Naumov
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorAlexey B. Dobrynin
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorDmitry B. Krivolapov
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorIgor A. Litvinov
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorOleg G. Sinyashin
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorCorresponding Author
Andrey A. Karasik
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian FederationSearch for more papers by this authorAnna S. Balueva
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorElvira I. Moussina
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorRoman N. Naumov
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorAlexey B. Dobrynin
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorDmitry B. Krivolapov
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorIgor A. Litvinov
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorOleg G. Sinyashin
A. E. Arbuzov Institute of Organic and Physical Chemistry, Russian Academy of Sciences, Kazan Scientific Center Arbuzov str. 8, Kazan 420088, Russian Federation
Search for more papers by this authorAbstract
The novel type of seven-membered cyclic diphosphines, namely 1,3,6-azadiphosphacycloheptanes, has been synthesized by condensation of 1,2-bis(phenylphosphino)ethane, formaldehyde, and primary amines (aniline, p-toluidine, benzylamine, and 5-aminoisophthalic acid) as a mixture of rac- and meso-stereoisomers. The structures of rac-stereoisomers of N-tolyl and N-(3′,5′-dicarboxyphenyl)-substituted diphosphines were investigated by X-ray crystal structure analyses. The stereoisomers of N-(3′,5′-dicarboxyphenyl)-substituted compound were separated at a preparative scale, and their platinum(II) dichloride complexes were obtained. The corresponding meso-isomer readily forms P,P-chelate complex with [PtCl2(cod)], whereas the rac-stereoisomer forms oligomeric complex. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:125–132, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20397
REFERENCES
- 1(a) Beller, M.; Kumar, K. In Transition Metals for Organic Synthesis; M. Beller; C. Bolm; (Eds); Wiley-VCH: Berlin, 2004; Vol. 1, Ch. 2.1, pp. 29–55; (b) Au-Yeung, T. T.-L.; Chan, S.-S.; Chan, A. S. C. In Transition Metals for Organic Synthesis; M. Beller; C. Bolm; (Eds); Wiley-VCH: Berlin, 2004; Vol. 2, Ch. 1.1.2, pp. 14–27; (c) Ohkuma, T.; Noyori, R. In Transition Metals for Organic Synthesis; M. Beller; C. Bolm; (Eds); Wiley-VCH: Berlin, 2004; Vol. 2, Ch. 1.1.3, pp. 29–113.
- 2(a)
Stelzer, O.;
Rossenbach, S.;
Hoff, D. In
Aqueous-Phase Organometallic Catalysis;
B. Cornils;
W. A. Herrmann (Eds).;
VCH: Berlin,
2004; Ch. 3.2.1,
pp. 100–120;
10.1002/3527602488.ch3b Google Scholar(b) Goedheijt, M. S.; Kamer, P. C., Reek, N. H.; van Leeuwen, P. W. N. M. In Aqueous-Phase Organometallic Catalysis; B. Cornils; W. A. Herrmann (Eds).; VCH: Berlin, 2004; Ch. 3.2.2, pp. 121–136.
- 3 Mathey, F. In Phosphorus-Carbon Heterocyclic Chemistry: The Rise of a New Domain; F. Mathey; (Ed); Pergamon: London, 2001; Ch. 1, pp. 1–15.
- 4 Hackney, M. L. J.; Schubert, D. M.; Brandt, P. F.; Haltiwanger, R. C.; Norman, A. D. Inorg Chem 1997, 36, 1867–1872.
- 5
Pabel, M.;
Wild, S. B. In
Phosphorus-Carbon Heterocyclic Chemistry: The Rise of a New Domain;
F. Mathey (ed);
Pergamon: London,
2001;
Ch. 6.1, pp. 631–669.
10.1016/B978-008043952-5/50015-2 Google Scholar
- 6 Toto, S. D.; Arbuckle, B. W.; Bharadwaj, P. K.; Doi, J. T.; Musker, W. K. Phosphorus, Sulfur, Silicon, Relat Elem 1991, 56, 27–38.
- 7 Arbuckle, B. W.; Musker, W. K. Polyhedron 1991, 10, 415–419.
- 8 Märkl, G.; Jin, G. Yu.; Schörner, Ch. Tetrahedron Lett 1980, 21, 1409–1412.
- 9 Bobrov, S. V.; Karasik, A. A.; Sinyashin, O. G. Phosphorus, Sulfur, Silicon 1999, 144–146, 289–292.
- 10 Arbuzov, B. A.; Nikonov, G. N. Adv Heterocycl Chem 1994, 61, 59–140 and references therein.
- 11 Karasik, A. A.; Georgiev, I. O.; Musina, E. I.; Heinicke, J.; Sinyashin, O. G. Polyhedron 2001, 20, 3321–3331.
- 12 Karasik, A. A; Naumov, R. N.; Sinyashin, O. G.; Belov, G. P.; Novikova, H. V.; Lönnecke, P.; Hey-Hawkins, E. Dalton Trans 2003, 2209–2214.
- 13 Karasik, A. A.; Naumov, R. N.; Sommer, R.; Sinyashin, O. G.; Hey-Hawkins, E. Polyhedron 2002, 21, 2251–2256.
- 14 Kane, J. C.; Wong, E. H.; Yap, G. P. A.; Rheingold, A. L. Polyhedron 1999, 18, 1183–1188.
- 15 Karasik, A. A.; Bobrov, S. V.; Akhmetzyanov, A. I.; Naumov, R. N.; Nikonov, G. N.; Sinyashin, O. G. Koordinatzionnaya Khim 1998, 24, 530–535.
- 16 Issleib, K.; Oehhme, H.; Mohr, K. Z Chem 1973, 19, 139–141.
- 17
Märkl, G.;
Jin, G. Yu.
Tetrahedron Lett
1981, 22, 3467–3470.
10.1016/S0040-4039(01)81933-X Google Scholar
- 18 Arbuzov, B. A.; Erastov, O. A.; Romanova, I. P.; Efremov, Yu. Ya.; Musin, R. Z. Izv Akad Nauk SSSR, Ser Khim 1982, 440–443.
- 19 Berning, D. E.; Katti, K.; Barnes, C. L.; Volkert, W. A. J Am Chem Soc 1999, 121, 1658–1664.
- 20 Karasik, A. A.; Nikonov, G. N.; Dokuchaev, A. S.; Litvinov, I. A. Russ J Coord Chem 1994, 20, 300–303.
- 21 Karasik, A. A.; Krashilina, A. V.; Gubaidullin, A. T.; Litvinov, I. A.; Cherkasov, V. K.; Sinyashin, O. G.; Abakumov, G. A. Russ Chem Bull 2000, 49, 1782–1788.
- 22 Karasik, A. A.; Bobrov, S. V.; Nikonov, G. N.; Pisarevskii, A. P.; Litvinov, I. A.; Dokuchaev, A. S.; Struchkov, Yu. T.; Enikeev, K. M. Russ J Coord Chem 1995, 21, 574–584.
- 23 Khairullina, R. Z.; Karasik, A. A.; Musakova, E. Yu. Neftekhimiya, 1994, 34, 332–335.
- 24 Novikova, E. V.; Karasik, A. A.; Hey-Hawkins, E.; Belov, G. P. Russ J Coord Chem 2005, 31, 280–288.
- 25 Butler, I. R.; Licence, P.; Coles, S. J.; Hursthouse, M. B. J Organomet Chem 2000, 598, 103–107.
- 26 Henderickson, J. B. J Am Chem Soc 1964, 86, 4854–4866.
- 27 Henderickson, J. B. J Am Chem Soc 1967, 89, 7036–7043.
- 28 Samitov, Yu. Yu. Atlas spektrov YaMR prostranstvennyh izomerov; Izd. Kazanskogo Universita: Kazan, Russian Federation, 1978; pp. 8–24.
- 29 Alt, H. G.; Baumgartner, R. R.; Brune, H. A. Chem Ber 1986, 119, 1694–1703.
- 30 Swiegers, G. F.; Malefeste, T. J. Coord Chem Rev 2002, 225, 91–121.
- 31 Altomare, A.; Cascarano, G.; Giacovazzo, C.; Viterbo, D. Acta Crystallogr Sec A 1991, 47, 744–748.
- 32 Sheldrick, G. M. SHELXL97: A Computer Program for Crystal Structure Determination; University of Gottingen: Gottingen, Germany, 1997.
- 33 Farrugia, L. J. J Appl Cryst 1999, 32, 837–838.
- 34 Straver, L. H.; Schierbeek, A. J. MolEN Structure Determination System, Program Description, Vol. 1; Nonius B.V., Delft, 1994; p. 180.
- 35 Mastalerz, P. Roczniki Chem 1965, 39, 33–37.
