Catalysis with inorganic cations. VIII. Macrocyclic-yliden malonates: Synthesis, spectroscopic investigation, and metal perchlorate catalysis of the Diels-Alder reaction

Tetrahedron

Volumn 54, Issue 33, 1998, Pages 9581-9602

  Desimoni, Giovanni ^a   Faita, Giuseppe ^a   Ricci, Marina ^a   Righetti, PierPaolo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ACETONITRILE; BARIUM; DICHLOROMETHANE; MAGNESIUM PERCHLORATE; MALONIC ACID; PERCHLORATE; SODIUM;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0032514583     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00517-1     Document Type: Article

References (24)

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14. 12) Hedderwick, R.J.M.; Hibbert, F.; Gold, V. J. Chem. Soc., Perkin Trans. 1 1991, 811, and references therein.
15. 13) Habata, Y.; Fujishiro, F.; Akabori, A. J. Chem. Soc., Perkin Trans. 1 1996, 953.
16. 14) The absorbances of 10,11a are linearly related to the MP concentration; for 10a: r = 0.997 and p = 0.36; for 11a: r = 0.994 and p = 1.39.
17. 15) Also the vinylic β-carbon atom had signals broadened and strongly deshielded in the order 11a > 10a > 9a ≫ 8a, Δδ being respectively 5.05, 4.04, 1.56, and 0.33 ppm.
18. 6 and heated at 130 °C in a sealed tube, the corresponding exo adducts were observed together with the starting products 9,10b.
19. 1H-NMR spectra after 5-10 days.
20. 18) Bradshaw, J.S.; Izatt, R.M. Acc. Chem. Res. 1997, 30, 338; Izatt, R.M.; Pawlak, K.; Bradshaw, J.S. Chem. Rev. 1995, 95, 2529.
21. 18) Bradshaw, J.S.; Izatt, R.M. Acc. Chem. Res. 1997, 30, 338; Izatt, R.M.; Pawlak, K.; Bradshaw, J.S. Chem. Rev. 1995, 95, 2529.
22. 19) Among the different type-3 complexes involving two carbonyl groups and two ethereal oxygen atoms (Mg - tetrahedral) or four oxygen atoms (Mg - octahedral) Hyperchem-MM3 calculations strongly favour (63 vs 100 Kcal/mol) the complex depicted in Figure 5b. Only the dimeric structure has an higher stability (Figure 5a - 54 Kcal/mol).
23. 20) Corsico Coda, A.; Desimoni, G.; Faita, G.; Righetti, P.P.; Tacconi, G. Tetrahedron 1989, 45, 775.
24. 21) Schumacher, J.C. "Perchlorates - Their Properties, Manufacture, and Uses", ACS Monograph Series; Reinhold, New York, 1960.