Synthesis and characterization of oxygen-substituted pericydynes

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1190-1191

  Brake, Marc ^a   Enkelmann, Volker ^a   Bunz, Uwe H F ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001218607     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952087q     Document Type: Article

References (19)

1. Scott, L. T.; Cooney, M. J. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds; VCH: Weinheim, 1995; p 321, and therein cited references. Scott, L. T.; Cooney, M. J.; Johnels, D. J. J. Am. Chem. Soc. 1990, 112, 4054.
2. Scott, L. T.; Cooney, M. J. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds; VCH: Weinheim, 1995; p 321, and therein cited references. Scott, L. T.; Cooney, M. J.; Johnels, D. J. J. Am. Chem. Soc. 1990, 112, 4054.
3. Rubin, Y.; Kahr, M.; Knobler, C. B.; Wilkins, L. J. Am, Chem. Soc. 1991, 113, 495.
4. (b) Diederich, F. In Modern Acetylene Chemistry; Stang, P. J., Diederich, P., Eds; VCH: Weinheim, 1995; p 444 and therein cited references,
5. (c) Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1994, 33, 1073.
6. (a) Hay, A. S. J. Org. Chem. 1962, 27, 3320.
7. (b) Glaser, C. Chem. Ber. 1869, 2, 422.
8. (c) Kevelam, H J.; Jong, K. L.; Meinders, H. C.; Challa, G. Makromol. Chem. 1975, 176, 1369.
9. (a) Hauptmann, H. Tetrahedron Lett. 1975, 1931. Hauptmann, H. Tetrahedron 1976, 1293.
10. (a) Hauptmann, H. Tetrahedron Lett. 1975, 1931. Hauptmann, H. Tetrahedron 1976, 1293.
11. (b) An, Y.-Z.; Rubin, Y.; Schaller, C.; Mc Elevany, S. W. J. Org. Chem. 1994, 59, 2927.
12. 2Si: C, 71.19; H, 10.06. Found: C, 69.93; H, 9.84.
13. (a) Berscheid, R.; Vögtle, F. Synthesis 1992, 58. Vögtle assigns the enhanced yield of cyclizations compared to the classic Eglington conditions to a template effect of the acetonitrile.
14. 4: C, 73.59; H, 6.79. Found: C, 73.44; H, 6.84.
15. 14: C, 74.05; H, 6.21. Found: C, 74.80; H, 6.49.
16. 16: C, 74.05; H, 6.21. Found: C, 74.05; H, 6.23.
17. w = 0.066. The structure contains 3 mol of toluene per ring, from which one is disordered.
18. de Meijere, A.; Kozhushkov, S.; Haumann, T.; Boese, R ; Puls, C.; Cooney, M. J.; Scott, L. T. Chem. Eur. J. 1995, I, 124 and therein cited references.
19. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.