Abstract
A new and simple approach to the analysis of pericyclic reactions based on combination of the interaction of HOMO-LUMO molecular orbitals and Huckel-Mobius aromaticity concept in transition state is reported. This approach seems to be more powerful than the Woodward-Hoffmann approach which appears to be limited to reactions with sufficiently high symmetry, and the Huckel-Mobius that use the non-participating lowest basis set (Ψ1). One important impact of the current approach is its capability in addressing the photochemical concerted reactions.
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References
R.B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry, Academic Press: New York, (1970).
S. Sankaraman, Pericyclic Reactions, Wiley-VCH, Weinheim, (2005).
R.B. Woodward, R. Hoffmann, J. Am. Chem. Soc. 87 (1965) 395.
R.B. Woodward, R. Hoffmann, J. Am. Chem. Soc. 87 (1965) 2046.
R.B. Woodward, R. Hoffmann, J. Am. Chem. Soc. 87 (1965) 2511.
R. Hoffmann, R.B. Woodward, Acc. Chem. Res. 1 (1968) 17.
K. Fukui, Theory of Orientation and Stereoselection, Springer Verlag: Berlin, (1967).
H.E. Zimmerman, Acc. Chem. Res. 4 (1971) 272.
K. Fukui, H. Fujimoto, Mechanisms of Molecular Migrations, Thyagarajan BS (ed), Interscience: New York, Vol. 2 (1968) 117.
K. Fukui, Acc. Chem. Res. 4 (1971) 57.
K. Fukui, Angew. Chem. Int. Ed. Engl. 21 (1982) 801.
I. Fleming, Frontier Orbital and Organic Chemical Reactions, Wiley: London, (1978).
M.J.S. Dewar, The Molecular Orbital Theory of Organic Chemistry, McGraw-Hill: New York, (1969).
M.J.S. Dewar, Angew. Chem. Int. Ed. Engl. 10 (1971) 761.
R.B. Woodward, R. Hoffmann, Angew. Chem. Int. Ed. 8 (1969) 781.
W.T.A.M. Van der Lugt, L.J. Oosterhof, J. Am. Chem. Soc. 91 (1969) 6042.
M.J.S. Dewar, R.C. Dougherty, The PMO Theory of Organic Chemistry, Plenum: New York, (1975).
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Dedicated to Professor H. Firouzabadi, one of the founders of Ph.D. program in organic chemistry in Iran on the occasion of his 65th birthday and also his retirement
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Shaabani, A. Frontier orbitals aromaticity: A simple approach to the analysis of pericyclic reactions. JICS 5 (Suppl 1), S47–S53 (2008). https://doi.org/10.1007/BF03246488
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DOI: https://doi.org/10.1007/BF03246488