Doubly bridged biscyclopropenones, a new family of phanes

Journal of Organic Chemistry

Volumn 61, Issue 6, 1996, Pages 1946-1953

  Gleiter, Rolf ^a   Merger, Martin ^a   Altreuther, Annegret ^a   Irngartinger, Hermann ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AB INITIO CALCULATIONS; ALTERNATIVE ROUTES; CARBON ATOMS; CYCLOADDITION REACTION; DICHLOROCARBENE; HYDRIDE ABSTRACTION; IN-SITU; NEW SPECIES; ORBITALS; TRANSANNULAR INTERACTION;

CYCLOADDITION;

HYDROLYSIS;

EID: 0000066335     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9515539     Document Type: Article

References (54)

1. Itoh, S.; Fujise, Y.; Fukazawa, Y. Cyclophanes; Academic Press, Inc.: New York, 1983; Vol. II, p 485.
2. Vögtle, F. Cyclophanchemie; Teubner: Stuttgart, 1990; p 155.
3. Haenel, M. W. Tetrahedron Lett. 1976, 3121.
4. O'Conner, J. G.; Keehn, P. M. Tetrahedron Lett. 1977, 3711.
5. Harmon, R. E.; Suder, R.; Gupta, S. K. J. Chem. Soc., Perkin Trans. 1 1972, 1746.
6. Gleiter, R.; Merger, M. Tetrahedron Lett. 1992, 33, 3473.
7. Gleiter, R.; Merger, M.; Oeser, T.; Irngartinger, H. Tetrahedron Lett. 1995, 36, 6425.
8. Gleiter, R.; Merger, M. Synthesis 1995, 696.
9. Gleiter, R.; Merger, M.; Altreuther, A.; Irngartinger, H. J. Org. Chem. 1995, 60, 4692.
10. Dahn, H.; Ung-Truong, M.-N. Helv. Chim. Acta 1987, 70, 2130.
11. Budzelaar, P. H. M.; Kraka, E.; Cremer, D.; Schleyer, P.v.R. J. Am. Chem. Soc. 1986, 108, 561.
12. Greenberg, A.; Tomkins, R. P. T.; Drobovolny, M.; Liebmann, J. F. J. Am. Chem. Soc. 1983, 105, 6855.
13. Dehmlow, E. V. Chem. Ber. 1967, 100, 3829.
14. Dehmlow, E. V. Tetrahedron Lett. 1965, 4003.
15. Breslow, R.; Altman, L. J.; Krebs, A.; Mohacsi, E.; Murata, I.; Peterson, R. A.; Posner, J. J. Am. Chem. Soc. 1965, 87, 1326.
16. Breslow, R.; Peterson, R. J. Am. Chem. Soc. 1960, 82, 4426.
17. Breslow, R.; Höver, H.; Chang, H. W. J. Am. Chem. Soc. 1962, 84, 3168.
18. Dauben, H. J.; Honnen, L. R.; Harmon, K. M. J. Org. Chem. 1960, 25, 1442.
19. Baird, M. S. 1-Halo- and 1,2-Dihalocyclopropenes, Useful Synthetic Intermediates in: Advances in Strain in Organic Chemistry; JAI Press: Greenwich, 1991; Vol. I, p 65-116.
20. Halton, B.; Banwell, M. G. Cyclopropenes In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1987; Part II, Chapter 21, pp 1236.
21. White, J. M.; Bromley, M. K. Tetrahedron Lett. 1993, 34, 4091.
22. Banwell, M. G.; Corbett, M.; Gulbis, J.; Mackay, M. F. J. Chem. Soc. Perkin Trans 1, 1993, 945.
23. Wittwer, W. Thesis, Universität Heidelberg, 1995.
24. Hart, D. W.; Blackburn, T. F.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 679.
25. Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
26. Dehmlow, E. V.; Stiehm, T. Angew. Chem. Int. Ed. Engl. 1987, 26, 329.
27. Dehmlow, E. V. Angew. Chem. Int. Ed. Engl. 1974, 13, 170.
28. Baird, M. S.; Nethercott, W.; Slowey, P. D. J. Chem. Res., Synop. 1985, 370;
29. J. Chem. Res., Miniprint 1985, 3815.
30. Baird, M. S.; Hussain, H. H.; Nethercott, N. J. Chem. Soc. Perkin Trans. 1 1986, 1845.
31. Baird, M. S.; Fitton, H. L.; Clegg, W.; McCamley, A. J. Chem. Soc., Perkin Trans 1 1993, 321.
32. Keller, E. SCHAKAL92, Kristallographisches Institut der Universität, D-79104 Freiburg i.Br., 1993.
33. Gleiter, R.; Karcher, M.; Jahn, R.; Irngartinger, H. Chem. Ber. 1988, 121, 735.
34. Heilbronner, E.; Bock, H. Das HMO-Modell und seine Anwendung; Verlag Chemie: Weinheim, 1968.
35. Dewar, M. J. S.; Dougherty, R. C. The PMO Theory of Organic Chemistry; Plenum Press: New York, 1975.
36. Gaussian 92, Revision G.1: Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian, Inc., Pittsburgh PA, 1992.
37. Hoffmann, R.; Imamura, A.; Hehre, W. J. J. Am. Chem. Soc. 1968, 90, 1499.
38. Reviews: Hoffmann, R. Acc. Chem. Res. 1971, 4, 1.
39. Gleiter, R. Angew. Chem. Int. Ed. Engl. 1974, 13, 696.
40. Paddon-Row, M. N. Acc. Chem. Res. 1982, 15, 245.
41. Martin, H. D.; Mayer, B. Angew. Chem. Int. Ed. Engl. 1983, 22, 283.
42. Gleiter, R.; Schäfer, W. Acc. Chem. Res. 1990, 23, 369 and references cited therein.
43. Bischof, P. MOLEK9000, Universität Heidelberg, 1995.
44. G92NBO, Version 3.1: Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weinhold, F. Theoret.Chem.Inst. and Dept.of Chem., Univ. of Wisconsin, Madison, WI. Paddon-Row, M. N.; Jordan, K. D. in Modern Models of Bonding and Delocalization; Liebman, J. F., Greenberg, A., Eds.; Verlag Chemie: Weinheim, 1988; p 115.
45. Martin, H.-D.; Mayer, B. Angew. Chem. Int. Ed. Engl. 1983, 22, 283.
46. Gleiter, R.; Schäfer, W. Acc. Chem. Res. 1990, 23, 369.
47. Bingham, R. C.; Dewar, M. J. S.; Lo, D. H. J. Am. Chem. Soc. 1975, 97, 1285.
48. Bischof, P. J. Am. Chem. Soc. 1976, 98, 6844.
49. Gleiter, R.; Kratz, D.; Schäfer, W.; Schehlmann, V. J. Am. Chem. Soc. 1991, 113, 9258.
50. Gleiter, R.; Merger, R.; Treptow, B.; Wittwer, W.; Pflästerer, G. Synthesis 1993, 558.
51. Buchwald, S. L.; LaMaire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Tetrahedron Lett. 1987, 28, 3895.
52. MULTAN 11/82: Main, P.; Fiske, S. J.; Hull, S. E.; Lessinger, L., Germain, G.; Declercq, J.-P.; Woolfson, M. M. Department of Physics, University of York, York, England, 1982.
53. MolEN: Structure Determination System, Enraf-Nonius, Delft Instruments X-Ray Diffraction B. V., Delft, Niederlande, 1990.
54. The authors have deposited tables of crystallographic refinement parameters, atomic coordinates, and the thermal parameters of 10 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge, Crystallographic Data Centre, 12 Union Road, Cambridge, CB21EZ, UK.