Molybdenum-catalysed and -mediated cycloaddition reactions: Efficient synthesis of complex products from 1-oxa-1, 3-dienes and cyclotrienes or -tetraenes

Chemische Berichte

Volumn 130, Issue 4, 1997, Pages 453-462

  Schmidt, Thomas ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

1 oxa 1, 3 dienes; Catalysis; Cycloadditions; Molybdenum; Stereoselectivity

Indexed keywords

EID: 0041122497     PISSN: 00092940     EISSN: None     Source Type: Journal    
DOI: 10.1002/cber.19971300404     Document Type: Article

References (48)

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24. Th. Schmidt, Habilitation Thesis, University of Cologne 1992.
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27. - I7b' Th. Schmidt, F. Bienewald, R. Goddard, J. Chem. Soc., Chem. Commun. 1994, 1857-1858.
28. 3, Z = 4; u (Mo-Ka) = 6.46 cm, range for data collection 20max = 64°; o) scan; inex ranges: -36 ≤ h ≤ 36, 0 £k < 10, 0 s l £ 22; reflections collected 3953; independent reflections 3824; parameters 245; no absorption correction. Structure solution: heavy atom method, structure refinement: Full matrix least-squares on F, R = 0.026, RH. = 0.033 based on 3693 reflections with I > 2σ(7).
29. J. A. S. Howell, J. C. Kola, D. T. Dixon, P. M. Burkinshaw, M. J. Thomas, J. Organomet. Chem. 1984, 266, 83-96;
30. P. M. Burkinshaw, D. T. Dixon, J. A. S. Howell, J. Chem. Soc., Dalton Trans. 1980, 999-1004;
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33. Th. Schmidt, unpublished results.
34. H. Bircher, B. R. Bender, W. von Philipsborn, Mag. Res. Chem 1993, 31, 293-298.
35. -1, range for data collection 20max = 54.9°; w scan; index ranges: 0 ≤ h ≤ 10, 0 s k ≤ 15, 0 ≤ l ≤ 28; reflections collected 2302; independent reflections 2277; parameters 218; no absorption correction. Structure solution: heavy atom method, structure refinement: Full matrix least-squares on F, R = 0.033, Rn. = 0.044 based on 2185 reflections with / > 2a(7).
36. X-ray crystal analysis of 10: Single crystal from methanol; 0.04 x 0, 28 x 0.35 mm, Enraf-Nonius CAD4 diffractometer; Cu-A'a (graphite monochromator, X = 1.54178), empirical formula Ci7H24O, space group C2; unij cell dimensions: a = 15.037(2), b = 16.465(2), c = 12.702(2) A, β= 114.06(1)°; rfcalc = 1.13 g cm-3, V = 2871.4(6) A3, Z = 8; u (Cu-Aa) = 4.85 cm-r range for data collection 2Oma< = 75°; > scan; index ranges: -14 s h ≤ 14, -14 ≤ k s 14, Ö < l ≤ 16; reflections collected 6135; independent reflections 5867; parameters 324; no absorption correction. Structure solution: direct methods, structure refinement: Full matrix least-squares on F, R = 0.055, R = 0.061 based on 3714 reflections with / > 2a(7).
37. for the Karplus relationship, see: E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, J. Wiley & Sons, Inc., New York, 1994, p. 641-647;
38. M. Karplus, J. Pliys. Chem. 1959, 30, 11;
39. H. Conroy, Adv. Org. Chem. 1960, 2, 265.
40. [I5] X-ray crystal analysis of 16[22) : Sincle crystal from n-pentane/ diethyl ether (9:1); 0.12 x 0.32 x 0.36 mm, Enraf-Nonius CAD4 diffractometer; Cu-ATa (graphite monochromator, X = 1.54178), empirical formula C14H2oO, space group PI; unit cell.dimensions: a = 8.034(1), b = 10.682(1), c = 14.952(1) A, a = 102.41(1)°, P = ?8.43(1)0, y = 90.24(1)°; rfcalc = 1.10 g cm-3, V = 1238.8(2) A3, Z = 4; u (Cu-A'a) = 4.80 cm-', range for data collection 2Omal = 75°; co scan; index ranges: -11 s h s 11, -14 ≤ k ≤ 14, 0 s 1 s 19; reflections collected 5265; independent reflections 5077; parameters 271; no absorption correction. Structure solution: direct methods, structure refinement: Full matrix least-squares on F, R = 0.055, Ru. = 0.065 based on 3618 reflections with I > 2a(7).
41. Th. Schmidt, F. Bienewald, preliminary report at the 16th International Conference on Organometallic Chemistry, July 10-15, 1994, University of Sussex, UK.
42. Th. Schmidt, F. Bienewaid, R. Goddard, Chem. Der. 1996, 729, 305-311.
43. Th. Schmidt, F. Bienewald, unpublished results.
44. Th. Schmidt, F. Lutz, Chem. Ber. 1995, 128, 953-956.
45. pure cycloocta-l, 3, 5-triene is obtained from the mixture prepared according to réf. 21 by treatment with 3 mol% of (n6benzene)tricarbonylmolybdenum(O) at 80 °C.
46. W. Causing, G. VVilke, Angew. Chem. 1978, 90, 380;
47. Angew. Chem. Int. Ed. Engl. 1978, 77, 371.
48. Further details of the crystal structure investigations may be obtained from the Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftlich-technische Information mbH, D-76344 Eggenstein-Leopoldshafen (FRG), on quoting the depository number CSD-59390, the name of the author, and the journal citation.