Aromatic heterocycles XII. Semiempirical PM3 study of Diels-Alder cycloaddition reaction of substituted phosphabenzenes

[1] C. Elschenbroich, M. Nowotny, A. Behrendt, K. Harms, S. Wocadlo and J. Pebler: “Pentakis (η 1-phosphinine)iron: synthesis, structure and mode of formation”, J. Am. Chem. Soc., Vol. 116, (1994), pp. 6217–6219. http://dx.doi.org/10.1021/ja00093a02210.1021/ja00093a022Search in Google Scholar

[2] A.J. Ashe III and J.C. Colburn: “Molybdenum-Carbonyl Complexes of the Group 5 Heterobenzenes”, J. Am. Chem. Soc., Vol. 99, (1977), pp. 8099–8100. http://dx.doi.org/10.1021/ja00466a07810.1021/ja00466a078Search in Google Scholar

[3] C. Elschenbroich, J. Koch, J. Kroker, M. Winsch, W. Massa, G. Baum and G. Stork: “η 6-Coordination von unsubstituierten pyridine η 6-benzol(η 6-pyridin) chrom und bis(η 6-pyridin)chrom”, Chem. Ber., Vol. 121, (1988), pp. 1983. Search in Google Scholar

[4] K. Dimroth, R. Thamm und H. Kaletsch: “6π-Komplexe von pyridine-derivaten, synthesen und reactionen”, Z. Naturforsch., Vol. 39b, (1984), pp. 207–212. Search in Google Scholar

[5] P. Rosa, N. Mezailles, L. Ricard, F. Mathey, P. Le Floch, and Y. Jean: “Dianionic Iron and Ruthenium(2-) Biophosphinine Complexes: A Formal d10 Ruthenium Complex”, Angew. Chem. Int. Ed. Engl., Vol. 40, (2001), pp. 1251–1255. http://dx.doi.org/10.1002/1521-3773(20010401)40:7<1251::AID-ANIE1251>3.0.CO;2-H10.1002/1521-3773(20010401)40:7<1251::AID-ANIE1251>3.0.CO;2-HSearch in Google Scholar

[6] P. Le Floch and F. Mathey: “Transition Metals in Phosphinine Chemistry”, Coord. Chem. Rev., Vol. 179–180, (1998), pp. 771–791. Search in Google Scholar

[7] C. Elschenbroich, S. Voss, O. Schiemann, A. Lippek and K. Harms: “η 1-Coordination of phosphinine to chromium, molybdenum and tungsten”, Organometallics, Vol. 17, (1998), pp. 4417–4424. http://dx.doi.org/10.1021/om980487910.1021/om9804879Search in Google Scholar

[8] C. Elschenbroich, M. Nowotny, A. Behrendt, W. Massa, S. Wocadlo: “Tetrakis(η 1 phosphabenzene)nikel”, Angew. Chem. Int. Ed. Engl. Vol. 31, (1992), pp. 1343–1345. http://dx.doi.org/10.1002/anie.19921343110.1002/anie.199213431Search in Google Scholar

[9] M. Mracec, M. Mracec, and Z. Simon: “X Aromatic Heterocycles. PM3 and HMO Study on the Diels-Alder Reactions of λ3-Heterobenzenes of The 15th Group”, Revue Roumaine de Chimie, Vol.45, (2000), pp. 1021–1025. Search in Google Scholar

[10] C. Batich, E. Heilbronner, V. Hornung, A.J. Ashe III, D.T. Clark, K.T. Cobley, D. Kilcast and I. Scanlan: “Photoelectron spectra of Phosphabenzene, Arsabenzene and Stibabenzene”, J. Am. Chem. Soc., Vol. 95, (1973), pp. 928. http://dx.doi.org/10.1021/ja00784a05410.1021/ja00784a054Search in Google Scholar

[11] A.J. Ashe III: “The group V heterobenzenes”, Acc. Chem. Res., Vol. 11, (1978), pp. 153. http://dx.doi.org/10.1021/ar50124a00510.1021/ar50124a005Search in Google Scholar

[12] G. Märkl and A. Merz: “Zur unsetzung des phosphabenzolsystem mit carbenen und carbenoiden”, Tetrahedron Letter, (1971), pp. 1269–1273. Search in Google Scholar

[13] L. Nyulaszi and G. Keglevich: “Study on the aromaticity and reactivity of chlorophosphinine”, Heteroat. Chem., Vol. 5, (1994), pp. 131–137. http://dx.doi.org/10.1002/hc.52005020910.1002/hc.520050209Search in Google Scholar

[14] G. Frisson, A. Sevin, N. Avarvari, F. Mathey and P. Le Floch: “The CH by N replacement effects on the aromaticity and reactivity of phosphinines”, J. Org. Chem., Vol. 64, (1999), pp. 5524–5529. http://dx.doi.org/10.1021/jo990361110.1021/jo9903611Search in Google Scholar

[15] H. Oehling, W. Schäfer and A. Schweig: “Sequence of highest occupied molecular orbital in the phosphorins system”, Angew. Chem.Int.Ed.Engl., Vol. 10, (1971), pp. 656–657. http://dx.doi.org/10.1002/anie.19710656110.1002/anie.197106561Search in Google Scholar

[16] G. Märkl: “2,4,6-Triphenylphosphabenzol”, Angew. Chem., Vol. 78, (1966), pp. 907. Search in Google Scholar

[17] K. Dimroth: Phosphorus Carbon Double Bonds, Springer-Verlag, Berlin, 1973. http://dx.doi.org/10.1007/BFb005136510.1007/BFb0051365Search in Google Scholar

[18] G. Märkl: “Phosphabenzol uns arsabenzol”, Chem. Unserer Zeit, Vol. 16, (1982), pp. 1939. http://dx.doi.org/10.1002/ciuz.1982016050310.1002/ciuz.19820160503Search in Google Scholar

[19] G. Märkl: “Aromatic Phosphorus Heterocycles”, Phosphorus and Sulfur, Vol. 3, (1977), pp. 77. Search in Google Scholar

[20] A.J.III Ashe and M.D. Gordon: “Bismabenzene. Diels-Alder Reaction of Group V Heteroaromatic with Hexafluorobutyne”, J. Amer. Chem. Soc., Vol. 94, (1972), pp. 7596. http://dx.doi.org/10.1021/ja00776a06310.1021/ja00776a063Search in Google Scholar

[21] G. Märkl and F. Lieb: “Substituierte 1-Phosphaberrelenes”, Angew. Chem., Vol. 80, (1968), pp. 702. Search in Google Scholar

[22] M. Alcaraz and F. Mathey: “Accroisment de la reactivite des phosphorines en tant que dienes et philodienes par complexation du phosphore”, Tetrahedron, Vol. 25, (1984), pp. 207. http://dx.doi.org/10.1016/S0040-4039(00)99841-110.1016/S0040-4039(00)99841-1Search in Google Scholar

[23] R. Stutmann: “A simple model for substituent effects in cycloaddition reaction”, Tetrahedron Lett., Vol. 29, (1971), pp. 2721–2724. http://dx.doi.org/10.1016/S0040-4039(01)96962-X10.1016/S0040-4039(01)96962-XSearch in Google Scholar

[24] G. Märkl, F. Lieb and C. Martin: “Substituierte benzo-phosphabarrelenes zur umsetzung von phosphabenzolen mit arinen”, Tetrahedron Lett, Vol. 13, (1971), pp. 1249. http://dx.doi.org/10.1016/S0040-4039(01)96678-X10.1016/S0040-4039(01)96678-XSearch in Google Scholar

[25] R.B. Woodward and R. Hoffmann: The conservation of orbital symmetry, Chemie Verlag, Weinheim, 1970. 10.1016/B978-1-4832-3290-4.50006-4Search in Google Scholar

[26] R. Hoffmann, R.B. Woodward: “Selection rules for concerted cycloaddition reaction”, J. Am. Chem. Soc., Vol. 87, (1965), pp. 2046–2048. http://dx.doi.org/10.1021/ja01087a03410.1021/ja01087a034Search in Google Scholar

[27] Hyper Chem Professional for Windows, Release 5.11, Hypercube Inc., Gainesville, Fl. 32601, USA, 1997. Search in Google Scholar

[28] M.J.S. Dewar, E.G. Zoldbush, E.F. Haley and J.J.P. Steward: “AM1, a new general purpose quantum mechanical molecular model”, J. Am. Chem. Soc., Vol. 107, (1985), pp. 3902–3909. http://dx.doi.org/10.1021/ja00299a02410.1021/ja00299a024Search in Google Scholar