Studies in the cycloproparene series: Cross-conjugated π-extended alkylidenecycloproparenes

European Journal of Organic Chemistry

Volumn , Issue 17, 2004, Pages 3707-3713

  Dixon, G M ^a   Halton, B ^a  

^a VICTORIA UNIVERSITY OF WELLINGTON   (New Zealand)

Author keywords

Arenes; Dipole moments; Hydrocarbons; Peterson olefination; Small ring systems; Strained molecules

Indexed keywords

CYCLOPENTANONE DERIVATIVE; CYCLOPROPANE DERIVATIVE; KETONE DERIVATIVE; NAPHTHALENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CALCULATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CONJUGATION; DIPOLE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 4544250792     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400353     Document Type: Article

References (44)

1. B. Halton, C. J. Randall, G. J. Gainsford, P. J. Stang, J. Am. Chem. Soc. 1986, 108, 5949-5956.
2. B. Halton, A. J. Kay, Z. Zhi-mei, R. Boese, T. Haumann, J. Chem. Soc., Perkin Trans. 1 1996, 1445-1452.
3. B. Halton, R. Boese, G. M. Dixon, Eur. J. Org. Chem. 2003, 4507-4512.
4. B. Halton, P. J. Stang, Synlett 1997, 145-158.
5. B. Halton, C. J. Randall, P. J. Stang, J. Am. Chem. Soc. 1984, 106, 6108-6110.
6. B. Halton, S. J. Buckland, Q. Lu, Q. Mei, P. J. Stang, J. Org. Chem. 1988, 53, 2418-2422.
7. B. Halton, Q. Lu, P. J. Stang, J. Chem. Soc., Chem. Commun. 1988, 879-880.
8. Y. Apeloig, R. Boese, D. Bläser, B. Halton, A. H. Maulitz, J. Am. Chem. Soc. 1998, 120, 10147-10153.
9. B. Halton, Q. Lu, W. H. Melhuish, J. Photochem. Photobiol., A: Chem. 1990, 52, 205-208.
10. B. Halton, Chem. Rev. 2003, 103, 1327-1370.
11. B. Halton, C. S. Jones, D. Margetic, Tetrahedron 2001, 57, 3529-3536.
12. B. Halton, C. S. Jones, P. T. Northcote, R. Boese, Aust. J. Chem. 1999, 52, 285-290.
13. B. Halton, C. S. Jones, Eur. J. Org. Chem, 2004, 138-146.
14. G. M. Dixon, PhD thesis, Victoria University of Wellington, New Zealand, 2002.
15. B. Halton, M. J. Cooney, T. W. Davey, G. S. Forman, Q. Lu, R. Boese, D. Bläser, A. H. Maulitz, J. Chem. Soc., Perkin Trans. 1 1995, 2819-2827.
16. A. Hinchliffe, H. J. S. Machado, Int. J. Mol. Sci. 2000, 1, 39-48.
17. A. P. Scott, I. Agranat, P. U. Biedermann, N. V. Riggs, L. Radom, J. Org. Chem. 1997, 62, 2026-2038.
18. J. Daub, L. W. Jenneskens, Chimia 1987, 41, 52-59.
19. M. Neuenschwander, Pure Appl. Chem. 1986, 58, 55-66.
20. M. Hanack, K. Ritter, I. Stein, W. Miller, Tetrahedron Lett. 1986, 27, 3357-3360.
21. B. Halton, R. Boese, G. M. Dixon, Tetrahedron Lett. 2004, 45, 2167-2170.
22. K. Ogawa, T. Sano, S. Yoshimura, K. Toriumi, J. Am. Chem. Soc. 1992, 114, 1041-1051.
23. M. Olomucki, J. Y. Le Gall, Bull. Soc. Chim. Fr. 1976, 1467-1468.
24. H. Frey, G. Behmann, G. Kaupp, Chem. Ber. 1987, 120, 387-393.
25. N. Marcotte, S. Fery-Forgues, J. Photochem. Photobiol. A 2000, 130, 133-138.
26. N. Marcotte, S. Fery-Forgues, S. Lavabre, S. Marguet, V. G. Pivovarenko, J. Phys. Chem. A 1999, 103, 3163-3170; N. Marcotte, S. Fery-Forgues, J. Chem. Soc., Perkin Trans. 2 2000, 1711-1716.
27. N. Marcotte, S. Fery-Forgues, S. Lavabre, S. Marguet, V. G. Pivovarenko, J. Phys. Chem. A 1999, 103, 3163-3170; N. Marcotte, S. Fery-Forgues, J. Chem. Soc., Perkin Trans. 2 2000, 1711-1716.
28. See e.g.: T. Hoshi, T. Kawashima, J. Okubo, M. Yamamoto, H. Inoue, J. Chem. Soc., Perkin Trans. 2 1986, 1147-1150; H. Tanaka, K. Yamada, H. Kawazura, J. Chem. Soc., Perkin Trans. 2 1978, 231-235, and refs cited.
29. See e.g.: T. Hoshi, T. Kawashima, J. Okubo, M. Yamamoto, H. Inoue, J. Chem. Soc., Perkin Trans. 2 1986, 1147-1150; H. Tanaka, K. Yamada, H. Kawazura, J. Chem. Soc., Perkin Trans. 2 1978, 231-235, and refs cited.
30. G. Venkateshwarlu, B. Subrahmanyam, Proc. Indian Acad. Sci. 1987, 99, 419-424; G. Venkateshwarlu, B. Subrahmanyam, Proc. Indian Acad. Sci. 1990, 102, 45-50.
31. G. Venkateshwarlu, B. Subrahmanyam, Proc. Indian Acad. Sci. 1987, 99, 419-424; G. Venkateshwarlu, B. Subrahmanyam, Proc. Indian Acad. Sci. 1990, 102, 45-50.
32. J. E. Dubois, W. V. Wright, Tetrahedron Lett. 1967, 3101-3106; B. M. Webster, Prog. Stereochem. 1958, 2, 99.
33. J. E. Dubois, W. V. Wright, Tetrahedron Lett. 1967, 3101-3106; B. M. Webster, Prog. Stereochem. 1958, 2, 99.
34. G. Wypych, Handbook of Solvents, Chem. Tec., Toronto, 2001.
35. Q. Lu, PhD thesis, Victoria University of Wellington, New Zealand, 1989.
36. recorded (2) For 16: [y × 1.73] + [(1 - y) × 1.73/0.79] = 2.06; with y = 0.283 and s-cis,s-cis/s-cis,s-trans = 28:72.
37. D. D. Perrin, W. L. F. Aramarego, D. R. Perrin, Purification of Laboratory Chemicals, 2nd ed., Pergamon, London, 1980.
38. E. A. Guggenheim, Trans. Faraday Soc. 1949, 45, 714-720.
39. J. W. Smith, Trans. Faraday Soc. 1950, 394-399.
40. C. R. Conrad, M. A. Dolliver, Org. Synth. 1932, 12, 22-24.
41. S. Watanasin, W. S. Murphy, Synthesis 1980, 647-650.
42. J. M. Eisenhart, A. B. Ellis, J. Org. Chem. 1985, 50, 4108-4113.
43. S. Spange, A. Seifert, H. Muller, S. Hesse, C. Jager, Angew. Chem. Int. Ed. 2002, 41, 1729-1732; P. J. Mitchell, L. Phillips, S. J. Roberts, V. Wray, Org. Magn. Reson. 1974, 6, 126-127.
44. S. Spange, A. Seifert, H. Muller, S. Hesse, C. Jager, Angew. Chem. Int. Ed. 2002, 41, 1729-1732; P. J. Mitchell, L. Phillips, S. J. Roberts, V. Wray, Org. Magn. Reson. 1974, 6, 126-127.