Reactivity Comparison of D–Glucose–Derived Dienophiles. Analysis of the Conformational and Electronic Properties 英文参考文献.docVIP

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Reactivity Comparison of D–Glucose–Derived Dienophiles. Analysis of the Conformational and Electronic Properties 英文参考文献.doc

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Reactivity Comparison of D–Glucose–Derived Dienophiles. Analysis of the Conformational and Electronic Properties 英文参考文献

451 Molecules 2000, 5 Reactivity Comparison of D–Glucose–Derived Dienophiles. Analysis of the Conformational and Electronic Properties S. C. Pellegrinet1, M. T. Baumgartner2 and R.A. Spanevello1 1Instituto de Química Orgánica de Síntesis (IQUIOS)- CONICET; Facultad de Ciencias Bioquímicas y Farmacéuticas-U.N.R. Suipacha 531, Rosario (2000), Argentina E-mail: iquiosra@citynet.net.ar 2INFIQC - Departamento de Químíca Orgánica, Fac. Ciencias Químicas- U.N.C. Ciudad Universitaria, (5000) Córdoba, Argentina E-mail: tere@dqo.fcq.unc.edu.ar Abstract: Semiempirical calculations were performed to carry out a conformational analysis for carbohydrate-derived dienophiles 1-4. For α,β-unsaturated carbonylic compounds 2-4, a good correlation between Diels-Alder reactivity with calculated values for LUMO energies was observed. Introduction As part of our studies on the Diels–Alder reactions of D–glucose–derived dienophiles with cyclo- pentadiene,[1,2] we undertook a theoretical investigation on the conformational and electronic prop- erties of the dienophilic structures 1-4. O OCH3 O OCH3 H O O H5C6 O H5C6 O EWG EWG 1, EWG=CN 2, EWG=CHO 3, EWG=C(O)CH 4, EWG=C(O)CH CH3 3 2 The application of the frontier molecular orbital theory could be of interest since the reactivity of the dienophiles in normal Diels–Alder reaction could be correlated with their LUMO energies. This kind of theoretical treatment has been used to make important qualitative studies on the reactivity and outcome of cycloaddition reactions in different dienophilic systems, including some sugar–derived di- enophiles.[3] 452 Molecules 2000, 5 Experimental The search for the minimum on the potential energy surface for the dienophiles 1-4 and cyclopenta- diene were carried out using the semiempirical program AMPAC version 2.1. The calculations were performed at the Restricted Hartree–Fock (RHF) AM1 level of theory. The stationary points were ob- tained through adequate