Towards acyclic 1,1-linked polycyclobutanes as potential precursors of polyspiranes with a helical primary structure: Synthesis of tercyclobutanes and attempted synthesis of quinquecyclobutanes

Tetrahedron

Volumn 55, Issue 13, 1999, Pages 3905-3916

  Gaini Rahimi, Said ^a   Steeneck, Christoph ^a   Meyer, Imelda ^a   Fitjer, Lutz ^a   Pauer, Frank ^a   Noltemeyer, Mathias ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033605838     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00098-8     Document Type: Article

References (25)

1. 1. For cyclic 1,l-linked polycyclobutanes (rotanes; m = 3,4,5,6), see: Fitjer, L.; Steeneck, C.; Gaini-Rahimi, S.; Schröder, U.; Justus, K.; Puder, P.; Dittmer, M.; Hassler, C.; Weiser, J.; Noltemeyer, M.; Teichert, M. J. Am. Chem. Soc. 1998, 120, 317-328.
2. The calculations were performed using the conformational search program HUNTER (Weiser, J.; Holthausen, M. C.; Fitjer, L. J. Comput. Chem. 1997, 18, 1264-1281) in connection with MM3(92) (Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8851-8856). A Unix version of HUNTER connected with MM3(92) (QCPE # 674) may be obtained from the Quantum Chemistry Program Exchange (QCPE), University of Indiana, Bloomington, IN 47405.
3. The calculations were performed using the conformational search program HUNTER (Weiser, J.; Holthausen, M. C.; Fitjer, L. J. Comput. Chem. 1997, 18, 1264-1281) in connection with MM3(92) (Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. J. Am. Chem. Soc. 1989, 111, 8851-8856). A Unix version of HUNTER connected with MM3(92) (QCPE # 674) may be obtained from the Quantum Chemistry Program Exchange (QCPE), University of Indiana, Bloomington, IN 47405.
4. For other approaches to helical polyspiranes (helixanes), see: (a) Gange, D.; Magnus, P.; Bass, L.; Arnold, E. V.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 2134-2135.
5. (b) Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1990, 112, 701-703.
6. (c) Hormuth, S.; Schade, W.; Reissig, H.-U. Liebigs Ann. 1996, 12, 2001-2006.
7. The number of possible diastereoisomers after hydrogenation is given in brackets.
8. Erickson, J. L. E.; Collins, Jr., F. E.; Owen, B. L. J. Org. Chem. 1966, 31, 481-484.
9. (a) Swan, G. A. J. Chem. Soc. 1948, 1408-1412.
10. (b) Gassmann, P. G.; Lumb, J. T.; Labar, F. V. J. Am. Chem. Soc. 1967, 89, 946-952.
11. (c) March, J.; Plankl, W. J. Chem. Sac. Perkin I 1977, 460-464.
12. (a) Cason, J.; Way, R. L. J. Org. Chem. 1949, 14, 31-36.
13. (b) Crich, D.; Barton, D. H. R.; Motherwell, W. W. Tetrahedron 1985, 41, 3901-3924; see also: Della, E. W.; Tsanaktsidis, J. Aust. J. Chem. 1989, 42, 61-69.
14. (b) Crich, D.; Barton, D. H. R.; Motherwell, W. W. Tetrahedron 1985, 41, 3901-3924; see also: Della, E. W.; Tsanaktsidis, J. Aust. J. Chem. 1989, 42, 61-69.
15. (c) Dupont, A. C.; Audia, V. H.; Waid, J. P.; Carter, J. P. Synth. Commun. 1990, 20, 1011-1021.
16. Fitjer, L.; Giersig, M.; Wehle, D.; Dittmer, M.; Koltermann, G.-W.; Schormann, N.; Egert, E. TetraheDron 1988, 393-404.
17. (a) Fitjer, L.; Giersig, M.; Clegg, W.; Schormann, N.; Sheldrick, G. M. Tetrahedron Lett. 1983, 24, 5351-5354.
18. (b) Giersig, M.; Wehle, D.; Fitjer, L.; Schormann, N.; Clegg, W. Chem. Ber. 1988, 121, 525-531.
19. 2 = 0.1213). All calculations were performed with the program SHELX TL. All relevant crystallographic data have been deposited with the Cambridge Crystallographic Data Centre. (equation presented)
20. quart).
21. Kohlrausch, K. W. F.; Skrabal, R. Monatsh. Chem. 1937, 70, 44-53.
22. Wright, S. W.; Hagemann, D. L.; Wright, A. S.; McClure, L. D. Tetrahedron Lett. 1997, 38, 7345-7348.
23. For the condensation of the closely related lithium tert-butyl isobutyrate with acid chlorides, see: Logue, M. J. Org. Chem. 1974, 39, 3455-3456.
24. For other successful high temperature methylenations, see: Fitjer, L.; Quabeck, U. Synth. Commun. 1985, 15, 855-864.
25. Utimoto, K.; Tamura, M.; Sisido, K. Tetrahedron 1973, 29, 1169-1171.