Chemistry of Conversions of [o-[1-Halo-1-(p-tolylsulfonyl)alkyl]benzyl]trimethylsilanes to o-Quinodimethanes and Benzocyclobutenes

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2086-2093

  Lenihan, Brian D ^a   Shechter, Harold ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000118550     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9705935     Document Type: Article

References (12)

1. (a) Lenihan, B. D.; Shechter, H. Tetrahedron Lett. 1994, 35, 7505.
2. (b) Lenihan, B. D.; Shechter, H. J. Org. Chem. 1998, 63, 2072.
3. Dechlorotrimethylsilylation of α-chlorosulfones is reported to be useful for synthesis of vinyl sulfones: (a) Hsiao, C.-N.; Shechter, H. J. Org. Chem. 1988, 53, 2688. (b) Hsiao, C. N.; Shechter, H. Tetrahedron Lett. 1982, 23, 3455.
4. Dechlorotrimethylsilylation of α-chlorosulfones is reported to be useful for synthesis of vinyl sulfones: (a) Hsiao, C.-N.; Shechter, H. J. Org. Chem. 1988, 53, 2688. (b) Hsiao, C. N.; Shechter, H. Tetrahedron Lett. 1982, 23, 3455.
5. For reviews of benzocyclobutenes and quinodimethanes, see ref 1 and its extensive references.
6. 4,6-Dimethylbenzocyclobutenyl p-tolyl sulfone has been prepared by pyrolysis of the sodium salt of 4,6-dimethylbenzocyclobutenone (p-toluenesulfonyl) hydrazone: (a) Blomquist, A. T.; Heins, C. F. J. Org. Chem. 1969, 34, 2906. α-Sulfonylbenzocyclobutenes can also be synthesized by ring closures involving benzyne intermediates: (b) Bunnett, J. F.; Skorcz, J. A. J. Org. Chem. 1962, 27, 3836. (c) Gowland, B. D.; Durst, T. Can. J. Chem. 1979, 57, 1462. (d) Iwao, M. J. Org. Chem. 1990, 55, 3622. Ring closure through benzyne intermediates is a general method for synthesis of 1-substituted benzocyclobutenes: (e) Skorcz, J. A.; Kaminski, F. E.; Williams, V. Z.; Wiberg, K. B. Org. Synth. Collect. Vol. V, 1973, 263. (f) Macdonald, D. I.; Durst, T. Tetrahedron Lett. 1986, 27, 2235. (g) Macdonald, D. I.; Durst, T. J. Org. Chem. 1988, 53, 3663.
7. 4,6-Dimethylbenzocyclobutenyl p-tolyl sulfone has been prepared by pyrolysis of the sodium salt of 4,6-dimethylbenzocyclobutenone (p-toluenesulfonyl) hydrazone: (a) Blomquist, A. T.; Heins, C. F. J. Org. Chem. 1969, 34, 2906. α-Sulfonylbenzocyclobutenes can also be synthesized by ring closures involving benzyne intermediates: (b) Bunnett, J. F.; Skorcz, J. A. J. Org. Chem. 1962, 27, 3836. (c) Gowland, B. D.; Durst, T. Can. J. Chem. 1979, 57, 1462. (d) Iwao, M. J. Org. Chem. 1990, 55, 3622. Ring closure through benzyne intermediates is a general method for synthesis of 1-substituted benzocyclobutenes: (e) Skorcz, J. A.; Kaminski, F. E.; Williams, V. Z.; Wiberg, K. B. Org. Synth. Collect. Vol. V, 1973, 263. (f) Macdonald, D. I.; Durst, T. Tetrahedron Lett. 1986, 27, 2235. (g) Macdonald, D. I.; Durst, T. J. Org. Chem. 1988, 53, 3663.
8. 4,6-Dimethylbenzocyclobutenyl p-tolyl sulfone has been prepared by pyrolysis of the sodium salt of 4,6-dimethylbenzocyclobutenone (p-toluenesulfonyl) hydrazone: (a) Blomquist, A. T.; Heins, C. F. J. Org. Chem. 1969, 34, 2906. α-Sulfonylbenzocyclobutenes can also be synthesized by ring closures involving benzyne intermediates: (b) Bunnett, J. F.; Skorcz, J. A. J. Org. Chem. 1962, 27, 3836. (c) Gowland, B. D.; Durst, T. Can. J. Chem. 1979, 57, 1462. (d) Iwao, M. J. Org. Chem. 1990, 55, 3622. Ring closure through benzyne intermediates is a general method for synthesis of 1-substituted benzocyclobutenes: (e) Skorcz, J. A.; Kaminski, F. E.; Williams, V. Z.; Wiberg, K. B. Org. Synth. Collect. Vol. V, 1973, 263. (f) Macdonald, D. I.; Durst, T. Tetrahedron Lett. 1986, 27, 2235. (g) Macdonald, D. I.; Durst, T. J. Org. Chem. 1988, 53, 3663.
9. 4,6-Dimethylbenzocyclobutenyl p-tolyl sulfone has been prepared by pyrolysis of the sodium salt of 4,6-dimethylbenzocyclobutenone (p-toluenesulfonyl) hydrazone: (a) Blomquist, A. T.; Heins, C. F. J. Org. Chem. 1969, 34, 2906. α-Sulfonylbenzocyclobutenes can also be synthesized by ring closures involving benzyne intermediates: (b) Bunnett, J. F.; Skorcz, J. A. J. Org. Chem. 1962, 27, 3836. (c) Gowland, B. D.; Durst, T. Can. J. Chem. 1979, 57, 1462. (d) Iwao, M. J. Org. Chem. 1990, 55, 3622. Ring closure through benzyne intermediates is a general method for synthesis of 1-substituted benzocyclobutenes: (e) Skorcz, J. A.; Kaminski, F. E.; Williams, V. Z.; Wiberg, K. B. Org. Synth. Collect. Vol. V, 1973, 263. (f) Macdonald, D. I.; Durst, T. Tetrahedron Lett. 1986, 27, 2235. (g) Macdonald, D. I.; Durst, T. J. Org. Chem. 1988, 53, 3663.
10. 4,6-Dimethylbenzocyclobutenyl p-tolyl sulfone has been prepared by pyrolysis of the sodium salt of 4,6-dimethylbenzocyclobutenone (p-toluenesulfonyl) hydrazone: (a) Blomquist, A. T.; Heins, C. F. J. Org. Chem. 1969, 34, 2906. α-Sulfonylbenzocyclobutenes can also be synthesized by ring closures involving benzyne intermediates: (b) Bunnett, J. F.; Skorcz, J. A. J. Org. Chem. 1962, 27, 3836. (c) Gowland, B. D.; Durst, T. Can. J. Chem. 1979, 57, 1462. (d) Iwao, M. J. Org. Chem. 1990, 55, 3622. Ring closure through benzyne intermediates is a general method for synthesis of 1-substituted benzocyclobutenes: (e) Skorcz, J. A.; Kaminski, F. E.; Williams, V. Z.; Wiberg, K. B. Org. Synth. Collect. Vol. V, 1973, 263. (f) Macdonald, D. I.; Durst, T. Tetrahedron Lett. 1986, 27, 2235. (g) Macdonald, D. I.; Durst, T. J. Org. Chem. 1988, 53, 3663.
11. 4,6-Dimethylbenzocyclobutenyl p-tolyl sulfone has been prepared by pyrolysis of the sodium salt of 4,6-dimethylbenzocyclobutenone (p-toluenesulfonyl) hydrazone: (a) Blomquist, A. T.; Heins, C. F. J. Org. Chem. 1969, 34, 2906. α-Sulfonylbenzocyclobutenes can also be synthesized by ring closures involving benzyne intermediates: (b) Bunnett, J. F.; Skorcz, J. A. J. Org. Chem. 1962, 27, 3836. (c) Gowland, B. D.; Durst, T. Can. J. Chem. 1979, 57, 1462. (d) Iwao, M. J. Org. Chem. 1990, 55, 3622. Ring closure through benzyne intermediates is a general method for synthesis of 1-substituted benzocyclobutenes: (e) Skorcz, J. A.; Kaminski, F. E.; Williams, V. Z.; Wiberg, K. B. Org. Synth. Collect. Vol. V, 1973, 263. (f) Macdonald, D. I.; Durst, T. Tetrahedron Lett. 1986, 27, 2235. (g) Macdonald, D. I.; Durst, T. J. Org. Chem. 1988, 53, 3663.
12. 4,6-Dimethylbenzocyclobutenyl p-tolyl sulfone has been prepared by pyrolysis of the sodium salt of 4,6-dimethylbenzocyclobutenone (p-toluenesulfonyl) hydrazone: (a) Blomquist, A. T.; Heins, C. F. J. Org. Chem. 1969, 34, 2906. α-Sulfonylbenzocyclobutenes can also be synthesized by ring closures involving benzyne intermediates: (b) Bunnett, J. F.; Skorcz, J. A. J. Org. Chem. 1962, 27, 3836. (c) Gowland, B. D.; Durst, T. Can. J. Chem. 1979, 57, 1462. (d) Iwao, M. J. Org. Chem. 1990, 55, 3622. Ring closure through benzyne intermediates is a general method for synthesis of 1-substituted benzocyclobutenes: (e) Skorcz, J. A.; Kaminski, F. E.; Williams, V. Z.; Wiberg, K. B. Org. Synth. Collect. Vol. V, 1973, 263. (f) Macdonald, D. I.; Durst, T. Tetrahedron Lett. 1986, 27, 2235. (g) Macdonald, D. I.; Durst, T. J. Org. Chem. 1988, 53, 3663.