Thermal Generation and Dimerization of [4]Metacyclophane

Journal of the American Chemical Society

Volumn 109, Issue 25, 1987, Pages 7887-7888

  Kostermans, Gerardus B M ^a   Van Dansik, Paul ^a   De Wolf, Willem H ^a   Bickelhaupt, Friedrich ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845281678     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00259a050     Document Type: Article

References (16)

1. For a recent review; see: Cyclophanes; Keehn, P. M.; Rosenfeld, S. M.; Eds.; Academic: New York, 1983.
2. Van Straten, J. W.; De Wolf, W. H.; Bickelhaupt, F. Tetrahedron Lett. 1977, 4667.
3. Jenneskens, L. W.; De Kanter, F. J. J.; Kraakman, P. A.; Turkenburg, L. A. M.; Koolhaas, W. E.; De Wolf, W. H.; Bickelhaupt, F.; Tobe, Y.; Kakiuchi, K.; Odaira, Y. J. Am. Chem. Soc. 1985, 107, 3716.
4. Rice, J. E.; Lee, T. J.; Remington, R. B.; Allen, W. D.; Clabo, D. A., Jr.; Schaefer, H. F., III. J. Am. Chem. Soc. 1987, 109, 2902.
5. Kostermans, G. B. M.; Bobeldijk, M.; De Wolf, W. H.; Bickelhaupt, F. J. Am. Chem. Soc. 1987, 109, 2471.
6. We thank Professor T. Tsuji for communicating his results prior to publication: Tsuji, T.; Nishida, S. J. Chem. Soc., Chem. Commun. 1987, 1189.
7. Kostermans, G. B. M.; Hogenbirk, M.; Turkenburg, L. A. M.; De Wolf, W. H.; Bickelhaupt. F. J. Am. Chem. Soc. 1987, 109. 2855.
8. Turkenburg, L. A. M.; Van Straten, J. W.; De Wolf, W. H.; Bickelhaupt, F. J. Am. Chem. Soc. 1980, 102, 3256.
9. Otsubo, T.; Kitasawa, M.; Misumi, S. Bull. Chem. Soc. Jpn. 1979, 52, 1515. Kaneda, T.; Otsubo, T.; Horita, H.; Misumi, S. Bull. Chem. Soc. Jpn. 1980, 53, 1015.
10. Martin, H. D.; Pfohler, P. Angew. Chem. 1978, 90, 901.
11. Yang, N. C.; Horner, M. G. Tetrahedron Lett. 1986, 27, 543. Yang, N. C.; Hrnjez, B. J.; Horner, M. G. J. Am. Chem. Soc. 1987, 109, 3158.
12. Higuchi, H.; Kobayashi, E.; Sakata, Y.; Misumi, S. Tetrahedron 1986, 42, 1731.
13. Jenneskens, L. W.; De Kanter, F. J. J.; De Wolf, W. H.; Bickelhaupt, F. J. Commit. Chem., in Dress.
14. Van Straten, J. W.; Turkenburg, L. A. M.; De Wolf, W. H.; Bickelhaupt, F. Recl. Trav. Chim. Pays-Bas 1985, 104, 89 and references cited.
15. The regiochemistry of the first step finds an analogy in the Diels-Alder reactions of [5]metacyclophane: Turkenburg, L. A. M.; Blok, P. M. L.; De Wolf, W. H.; Bickelhaupt, F. Angew. Chem. 1982, 94, 291. For a [4 + 2] addition analogous to the second step, see: Westberg, H. M; Cain. E. N.; Masamune, S. J. Am. Chem. Soc. 1969. 91. 7512.
16. The last one of these cycloreversions is analogous to the cleavage of o,p'-dibenzene into two benzene molecules: Braun, R.; Kummer, M.; Martin, H. D.; Rubin, M. B. Angew. Chem. 1985, 97, 1054.