A Facile Synthesis of Tetra- and Dihydronaphthalene Derivatives by Excimer Laser Photolysis of 1,2-Bis(substituted-methyl)benzenes in the Presence of Olefins and Acetylene

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7376-7383

  Ouchi, Akihiko ^a   Koga, Yoshinori ^a  

^a NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000187690     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970953o     Document Type: Article

References (62)

1. Reviews: (a) Kleinermanns, K.; Wolfrum, J. Angew. Chem., Int. Ed. Engl. 1987, 26, 38-58. (b) Wilson, R. M.; Schnapp, K. A.; Hannemann, K.; Ho, D. M.; Memarian, H. R.; Azadnia, A.; Pinhas, A. R.; Figley, T. M. Spectrochim. Acta, Part A 1990, 46, 551-558. (c) Wilson, R. M.; Adam, W.; Schulte Oestrich, R. Spectrum 1991, 4, 8-17. (d) Wilson, R. M.; Schnapp, K. A. Chem. Rev. 1993, 93, 223-249. (e) Johnston, L. J. Chem. Rev. 1993, 93, 251-266.
2. Reviews: (a) Kleinermanns, K.; Wolfrum, J. Angew. Chem., Int. Ed. Engl. 1987, 26, 38-58. (b) Wilson, R. M.; Schnapp, K. A.; Hannemann, K.; Ho, D. M.; Memarian, H. R.; Azadnia, A.; Pinhas, A. R.; Figley, T. M. Spectrochim. Acta, Part A 1990, 46, 551-558. (c) Wilson, R. M.; Adam, W.; Schulte Oestrich, R. Spectrum 1991, 4, 8-17. (d) Wilson, R. M.; Schnapp, K. A. Chem. Rev. 1993, 93, 223-249. (e) Johnston, L. J. Chem. Rev. 1993, 93, 251-266.
3. Reviews: (a) Kleinermanns, K.; Wolfrum, J. Angew. Chem., Int. Ed. Engl. 1987, 26, 38-58. (b) Wilson, R. M.; Schnapp, K. A.; Hannemann, K.; Ho, D. M.; Memarian, H. R.; Azadnia, A.; Pinhas, A. R.; Figley, T. M. Spectrochim. Acta, Part A 1990, 46, 551-558. (c) Wilson, R. M.; Adam, W.; Schulte Oestrich, R. Spectrum 1991, 4, 8-17. (d) Wilson, R. M.; Schnapp, K. A. Chem. Rev. 1993, 93, 223-249. (e) Johnston, L. J. Chem. Rev. 1993, 93, 251-266.
4. Reviews: (a) Kleinermanns, K.; Wolfrum, J. Angew. Chem., Int. Ed. Engl. 1987, 26, 38-58. (b) Wilson, R. M.; Schnapp, K. A.; Hannemann, K.; Ho, D. M.; Memarian, H. R.; Azadnia, A.; Pinhas, A. R.; Figley, T. M. Spectrochim. Acta, Part A 1990, 46, 551-558. (c) Wilson, R. M.; Adam, W.; Schulte Oestrich, R. Spectrum 1991, 4, 8-17. (d) Wilson, R. M.; Schnapp, K. A. Chem. Rev. 1993, 93, 223-249. (e) Johnston, L. J. Chem. Rev. 1993, 93, 251-266.
5. Reviews: (a) Kleinermanns, K.; Wolfrum, J. Angew. Chem., Int. Ed. Engl. 1987, 26, 38-58. (b) Wilson, R. M.; Schnapp, K. A.; Hannemann, K.; Ho, D. M.; Memarian, H. R.; Azadnia, A.; Pinhas, A. R.; Figley, T. M. Spectrochim. Acta, Part A 1990, 46, 551-558. (c) Wilson, R. M.; Adam, W.; Schulte Oestrich, R. Spectrum 1991, 4, 8-17. (d) Wilson, R. M.; Schnapp, K. A. Chem. Rev. 1993, 93, 223-249. (e) Johnston, L. J. Chem. Rev. 1993, 93, 251-266.
6. Laser-jet photolysis: e.g. (a) Wilson, R. M.; Romanova, T. N.; Azadnia, A.; Bauer, J. A. K.; Johnson, R. P. Tetrahedron Lett. 1994, 35, 5401-5404. (b) Adam, W.; Kita, F. J. Am. Chem. Soc. 1994, 116, 3680-3683. (c) Adam, W.; Kita, F.; Schulte Oestrich, R. J. Photochem. Photobiol. A 1994, 80, 187-197. (d) Adam, W.; Patterson, J. J. Org. Chem. 1995, 60, 7769-7773. (e) Wilson, R. M.; Patterson, W. S.; Austen, S. C.; Ho, D. M.; Bauer, J. A. K. J. Am. Chem. Soc. 1995, 117, 7820-7821. (f) Adam, W.; Walther, B. Tetrahedron 1996, 52, 10399-10404. (g) Schnapp, K. A.; Motz, P. L.; Stoeckel, S. M.; Wilson, R. M.; Bauer, J. A. K.; Bohne, C. Tetrahedron Lett. 1996, 37, 2317-2320.
7. Laser-jet photolysis: e.g. (a) Wilson, R. M.; Romanova, T. N.; Azadnia, A.; Bauer, J. A. K.; Johnson, R. P. Tetrahedron Lett. 1994, 35, 5401-5404. (b) Adam, W.; Kita, F. J. Am. Chem. Soc. 1994, 116, 3680-3683. (c) Adam, W.; Kita, F.; Schulte Oestrich, R. J. Photochem. Photobiol. A 1994, 80, 187-197. (d) Adam, W.; Patterson, J. J. Org. Chem. 1995, 60, 7769-7773. (e) Wilson, R. M.; Patterson, W. S.; Austen, S. C.; Ho, D. M.; Bauer, J. A. K. J. Am. Chem. Soc. 1995, 117, 7820-7821. (f) Adam, W.; Walther, B. Tetrahedron 1996, 52, 10399-10404. (g) Schnapp, K. A.; Motz, P. L.; Stoeckel, S. M.; Wilson, R. M.; Bauer, J. A. K.; Bohne, C. Tetrahedron Lett. 1996, 37, 2317-2320.
8. Laser-jet photolysis: e.g. (a) Wilson, R. M.; Romanova, T. N.; Azadnia, A.; Bauer, J. A. K.; Johnson, R. P. Tetrahedron Lett. 1994, 35, 5401-5404. (b) Adam, W.; Kita, F. J. Am. Chem. Soc. 1994, 116, 3680-3683. (c) Adam, W.; Kita, F.; Schulte Oestrich, R. J. Photochem. Photobiol. A 1994, 80, 187-197. (d) Adam, W.; Patterson, J. J. Org. Chem. 1995, 60, 7769-7773. (e) Wilson, R. M.; Patterson, W. S.; Austen, S. C.; Ho, D. M.; Bauer, J. A. K. J. Am. Chem. Soc. 1995, 117, 7820-7821. (f) Adam, W.; Walther, B. Tetrahedron 1996, 52, 10399-10404. (g) Schnapp, K. A.; Motz, P. L.; Stoeckel, S. M.; Wilson, R. M.; Bauer, J. A. K.; Bohne, C. Tetrahedron Lett. 1996, 37, 2317-2320.
9. Laser-jet photolysis: e.g. (a) Wilson, R. M.; Romanova, T. N.; Azadnia, A.; Bauer, J. A. K.; Johnson, R. P. Tetrahedron Lett. 1994, 35, 5401-5404. (b) Adam, W.; Kita, F. J. Am. Chem. Soc. 1994, 116, 3680-3683. (c) Adam, W.; Kita, F.; Schulte Oestrich, R. J. Photochem. Photobiol. A 1994, 80, 187-197. (d) Adam, W.; Patterson, J. J. Org. Chem. 1995, 60, 7769-7773. (e) Wilson, R. M.; Patterson, W. S.; Austen, S. C.; Ho, D. M.; Bauer, J. A. K. J. Am. Chem. Soc. 1995, 117, 7820-7821. (f) Adam, W.; Walther, B. Tetrahedron 1996, 52, 10399-10404. (g) Schnapp, K. A.; Motz, P. L.; Stoeckel, S. M.; Wilson, R. M.; Bauer, J. A. K.; Bohne, C. Tetrahedron Lett. 1996, 37, 2317-2320.
10. Laser-jet photolysis: e.g. (a) Wilson, R. M.; Romanova, T. N.; Azadnia, A.; Bauer, J. A. K.; Johnson, R. P. Tetrahedron Lett. 1994, 35, 5401-5404. (b) Adam, W.; Kita, F. J. Am. Chem. Soc. 1994, 116, 3680-3683. (c) Adam, W.; Kita, F.; Schulte Oestrich, R. J. Photochem. Photobiol. A 1994, 80, 187-197. (d) Adam, W.; Patterson, J. J. Org. Chem. 1995, 60, 7769-7773. (e) Wilson, R. M.; Patterson, W. S.; Austen, S. C.; Ho, D. M.; Bauer, J. A. K. J. Am. Chem. Soc. 1995, 117, 7820-7821. (f) Adam, W.; Walther, B. Tetrahedron 1996, 52, 10399-10404. (g) Schnapp, K. A.; Motz, P. L.; Stoeckel, S. M.; Wilson, R. M.; Bauer, J. A. K.; Bohne, C. Tetrahedron Lett. 1996, 37, 2317-2320.
11. Laser-jet photolysis: e.g. (a) Wilson, R. M.; Romanova, T. N.; Azadnia, A.; Bauer, J. A. K.; Johnson, R. P. Tetrahedron Lett. 1994, 35, 5401-5404. (b) Adam, W.; Kita, F. J. Am. Chem. Soc. 1994, 116, 3680-3683. (c) Adam, W.; Kita, F.; Schulte Oestrich, R. J. Photochem. Photobiol. A 1994, 80, 187-197. (d) Adam, W.; Patterson, J. J. Org. Chem. 1995, 60, 7769-7773. (e) Wilson, R. M.; Patterson, W. S.; Austen, S. C.; Ho, D. M.; Bauer, J. A. K. J. Am. Chem. Soc. 1995, 117, 7820-7821. (f) Adam, W.; Walther, B. Tetrahedron 1996, 52, 10399-10404. (g) Schnapp, K. A.; Motz, P. L.; Stoeckel, S. M.; Wilson, R. M.; Bauer, J. A. K.; Bohne, C. Tetrahedron Lett. 1996, 37, 2317-2320.
12. Laser-jet photolysis: e.g. (a) Wilson, R. M.; Romanova, T. N.; Azadnia, A.; Bauer, J. A. K.; Johnson, R. P. Tetrahedron Lett. 1994, 35, 5401-5404. (b) Adam, W.; Kita, F. J. Am. Chem. Soc. 1994, 116, 3680-3683. (c) Adam, W.; Kita, F.; Schulte Oestrich, R. J. Photochem. Photobiol. A 1994, 80, 187-197. (d) Adam, W.; Patterson, J. J. Org. Chem. 1995, 60, 7769-7773. (e) Wilson, R. M.; Patterson, W. S.; Austen, S. C.; Ho, D. M.; Bauer, J. A. K. J. Am. Chem. Soc. 1995, 117, 7820-7821. (f) Adam, W.; Walther, B. Tetrahedron 1996, 52, 10399-10404. (g) Schnapp, K. A.; Motz, P. L.; Stoeckel, S. M.; Wilson, R. M.; Bauer, J. A. K.; Bohne, C. Tetrahedron Lett. 1996, 37, 2317-2320.
13. Laser drop photolysis: (a) Banks, J. T.; Scaiano, J. C. J. Am. Chem. Soc. 1993, 115, 6409-6413. (b) Scaiano, J. C.; Banks, J. T. J. Braz. Chem. Soc. 1995, 6, 199-210. (c) Banks, J. T.; Scaiano, J. C. J. Phys. Chem. 1995, 99, 3527-3531. (d) Banks, J. T.; Scaiano, J. C. J. Photochem. Photobiol. A. 1996, 96, 31-33.
14. Laser drop photolysis: (a) Banks, J. T.; Scaiano, J. C. J. Am. Chem. Soc. 1993, 115, 6409-6413. (b) Scaiano, J. C.; Banks, J. T. J. Braz. Chem. Soc. 1995, 6, 199-210. (c) Banks, J. T.; Scaiano, J. C. J. Phys. Chem. 1995, 99, 3527-3531. (d) Banks, J. T.; Scaiano, J. C. J. Photochem. Photobiol. A. 1996, 96, 31-33.
15. Laser drop photolysis: (a) Banks, J. T.; Scaiano, J. C. J. Am. Chem. Soc. 1993, 115, 6409-6413. (b) Scaiano, J. C.; Banks, J. T. J. Braz. Chem. Soc. 1995, 6, 199-210. (c) Banks, J. T.; Scaiano, J. C. J. Phys. Chem. 1995, 99, 3527-3531. (d) Banks, J. T.; Scaiano, J. C. J. Photochem. Photobiol. A. 1996, 96, 31-33.
16. Laser drop photolysis: (a) Banks, J. T.; Scaiano, J. C. J. Am. Chem. Soc. 1993, 115, 6409-6413. (b) Scaiano, J. C.; Banks, J. T. J. Braz. Chem. Soc. 1995, 6, 199-210. (c) Banks, J. T.; Scaiano, J. C. J. Phys. Chem. 1995, 99, 3527-3531. (d) Banks, J. T.; Scaiano, J. C. J. Photochem. Photobiol. A. 1996, 96, 31-33.
17. Two-color, two-pulse photolysis: (a) Netto-Ferreira, J. C.; Wintgens, V.; Scaiano, J. C. Tetrahedron Lett. 1989, 30, 6851-6854. (b) Bendig, J.; Mitzner, R. Ber. Bunsen-Ges. Phys. Chem. 1994, 98, 1004-1008. (c) Ouchi, A.; Yabe, A. Chem. Lett. 1995, 945-946. (d) Ouchi, A.; Koga, Y. Tetrahedron Lett. 1995, 36, 8999-9002.
18. Two-color, two-pulse photolysis: (a) Netto-Ferreira, J. C.; Wintgens, V.; Scaiano, J. C. Tetrahedron Lett. 1989, 30, 6851-6854. (b) Bendig, J.; Mitzner, R. Ber. Bunsen-Ges. Phys. Chem. 1994, 98, 1004-1008. (c) Ouchi, A.; Yabe, A. Chem. Lett. 1995, 945-946. (d) Ouchi, A.; Koga, Y. Tetrahedron Lett. 1995, 36, 8999-9002.
19. Two-color, two-pulse photolysis: (a) Netto-Ferreira, J. C.; Wintgens, V.; Scaiano, J. C. Tetrahedron Lett. 1989, 30, 6851-6854. (b) Bendig, J.; Mitzner, R. Ber. Bunsen-Ges. Phys. Chem. 1994, 98, 1004-1008. (c) Ouchi, A.; Yabe, A. Chem. Lett. 1995, 945-946. (d) Ouchi, A.; Koga, Y. Tetrahedron Lett. 1995, 36, 8999-9002.
20. Two-color, two-pulse photolysis: (a) Netto-Ferreira, J. C.; Wintgens, V.; Scaiano, J. C. Tetrahedron Lett. 1989, 30, 6851-6854. (b) Bendig, J.; Mitzner, R. Ber. Bunsen-Ges. Phys. Chem. 1994, 98, 1004-1008. (c) Ouchi, A.; Yabe, A. Chem. Lett. 1995, 945-946. (d) Ouchi, A.; Koga, Y. Tetrahedron Lett. 1995, 36, 8999-9002.
21. Laser photolysis: e.g. (a) Alkenings, B.; Bettermann, H.; Dasting, I.; Schroers, H.-J. Vib. Spectrosc. 1993, 5, 43-49. (b) Pérez-Prieto, J.; Miranda, M. A.; Font-Sanchis, E.; Kónya, K.; Scaiano, J. C. Tetrahedron Lett. 1996, 37, 4923-4926. (c) Pérez-Prieto, J.; Miranda, M. A.; García, H.; Scaiano, J. C. J. Org. Chem. 1996, 61, 3773-3777. (d) Ouchi, A.; Koga, Y.; Adam, W. J. Am. Chem. Soc. 1997, 119, 592-599.
22. Laser photolysis: e.g. (a) Alkenings, B.; Bettermann, H.; Dasting, I.; Schroers, H.-J. Vib. Spectrosc. 1993, 5, 43-49. (b) Pérez-Prieto, J.; Miranda, M. A.; Font-Sanchis, E.; Kónya, K.; Scaiano, J. C. Tetrahedron Lett. 1996, 37, 4923-4926. (c) Pérez-Prieto, J.; Miranda, M. A.; García, H.; Scaiano, J. C. J. Org. Chem. 1996, 61, 3773-3777. (d) Ouchi, A.; Koga, Y.; Adam, W. J. Am. Chem. Soc. 1997, 119, 592-599.
23. Laser photolysis: e.g. (a) Alkenings, B.; Bettermann, H.; Dasting, I.; Schroers, H.-J. Vib. Spectrosc. 1993, 5, 43-49. (b) Pérez-Prieto, J.; Miranda, M. A.; Font-Sanchis, E.; Kónya, K.; Scaiano, J. C. Tetrahedron Lett. 1996, 37, 4923-4926. (c) Pérez-Prieto, J.; Miranda, M. A.; García, H.; Scaiano, J. C. J. Org. Chem. 1996, 61, 3773-3777. (d) Ouchi, A.; Koga, Y.; Adam, W. J. Am. Chem. Soc. 1997, 119, 592-599.
24. Laser photolysis: e.g. (a) Alkenings, B.; Bettermann, H.; Dasting, I.; Schroers, H.-J. Vib. Spectrosc. 1993, 5, 43-49. (b) Pérez-Prieto, J.; Miranda, M. A.; Font-Sanchis, E.; Kónya, K.; Scaiano, J. C. Tetrahedron Lett. 1996, 37, 4923-4926. (c) Pérez-Prieto, J.; Miranda, M. A.; García, H.; Scaiano, J. C. J. Org. Chem. 1996, 61, 3773-3777. (d) Ouchi, A.; Koga, Y.; Adam, W. J. Am. Chem. Soc. 1997, 119, 592-599.
25. Reactions from higher excited states: e.g. (a) Pola, J.; Taylor, R. Tetrahedron Lett. 1994, 35, 2799-2800. (b) Ichinose, N.; Kawanishi, S. J. Chem. Soc., Chem. Commun. 1994, 2017-2018. (c) North, S. W.; Blanck, D. A.; Gezelter, J. D.; Longfellow, C. A.; Lee, Y. T. J. Chem. Phys. 1995, 102, 4447-4460. (d) Kawamata, K.; Kikuchi, K.; Okada, K.; Oda, M. J. Phys. Chem. 1995, 99, 3548-3553.
26. Reactions from higher excited states: e.g. (a) Pola, J.; Taylor, R. Tetrahedron Lett. 1994, 35, 2799-2800. (b) Ichinose, N.; Kawanishi, S. J. Chem. Soc., Chem. Commun. 1994, 2017-2018. (c) North, S. W.; Blanck, D. A.; Gezelter, J. D.; Longfellow, C. A.; Lee, Y. T. J. Chem. Phys. 1995, 102, 4447-4460. (d) Kawamata, K.; Kikuchi, K.; Okada, K.; Oda, M. J. Phys. Chem. 1995, 99, 3548-3553.
27. Reactions from higher excited states: e.g. (a) Pola, J.; Taylor, R. Tetrahedron Lett. 1994, 35, 2799-2800. (b) Ichinose, N.; Kawanishi, S. J. Chem. Soc., Chem. Commun. 1994, 2017-2018. (c) North, S. W.; Blanck, D. A.; Gezelter, J. D.; Longfellow, C. A.; Lee, Y. T. J. Chem. Phys. 1995, 102, 4447-4460. (d) Kawamata, K.; Kikuchi, K.; Okada, K.; Oda, M. J. Phys. Chem. 1995, 99, 3548-3553.
28. Reactions from higher excited states: e.g. (a) Pola, J.; Taylor, R. Tetrahedron Lett. 1994, 35, 2799-2800. (b) Ichinose, N.; Kawanishi, S. J. Chem. Soc., Chem. Commun. 1994, 2017-2018. (c) North, S. W.; Blanck, D. A.; Gezelter, J. D.; Longfellow, C. A.; Lee, Y. T. J. Chem. Phys. 1995, 102, 4447-4460. (d) Kawamata, K.; Kikuchi, K.; Okada, K.; Oda, M. J. Phys. Chem. 1995, 99, 3548-3553.
29. Reactions by nonresonant two-photon excitation: (a) Kira, M.; Miyazawa, T.; Koshihara, S.; Segawa, Y.; Sakurai, H. Chem. Lett. 1995, 3-4. (b) Miyazawa, T.; Koshihara, S.; Segawa, Y.; Kira, M. Ibid. 1995, 217-218.
30. Reactions by nonresonant two-photon excitation: (a) Kira, M.; Miyazawa, T.; Koshihara, S.; Segawa, Y.; Sakurai, H. Chem. Lett. 1995, 3-4. (b) Miyazawa, T.; Koshihara, S.; Segawa, Y.; Kira, M. Ibid. 1995, 217-218.
31. (a) Ouchi, A.; Adam, W. J. Chem. Soc., Chem. Commun. 1993, 628-629.
32. (b) Ouchi, A.; Yabe, A.; Adam, W. Tetrahedron Lett. 1994, 35, 6309-6312.
33. (c) Reference 4d.
34. Reviews: (a) McCullough, J. J. Acc. Chem. Res. 1980, 13, 270-276. (b) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873-2889. (c) Scaiano, J. C.; Wintgens, V.; Netto-Ferreira, J. C. Pure Appl. Chem. 1990, 62, 1557-1564. (d) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237-272.
35. Reviews: (a) McCullough, J. J. Acc. Chem. Res. 1980, 13, 270-276. (b) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873-2889. (c) Scaiano, J. C.; Wintgens, V.; Netto-Ferreira, J. C. Pure Appl. Chem. 1990, 62, 1557-1564. (d) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237-272.
36. Reviews: (a) McCullough, J. J. Acc. Chem. Res. 1980, 13, 270-276. (b) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873-2889. (c) Scaiano, J. C.; Wintgens, V.; Netto-Ferreira, J. C. Pure Appl. Chem. 1990, 62, 1557-1564. (d) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237-272.
37. Reviews: (a) McCullough, J. J. Acc. Chem. Res. 1980, 13, 270-276. (b) Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873-2889. (c) Scaiano, J. C.; Wintgens, V.; Netto-Ferreira, J. C. Pure Appl. Chem. 1990, 62, 1557-1564. (d) Martin, N.; Seoane, C.; Hanack, M. Org. Prep. Proced. Int. 1991, 23, 237-272.
38. Reviews: (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16,10-23. (b) Oppolzer, W. Synthesis 1978, 793-802. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41-61. (d) Kametani, T.; Nemoto, H. Tetrahedron 1981, 37, 3-16.
39. Reviews: (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16,10-23. (b) Oppolzer, W. Synthesis 1978, 793-802. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41-61. (d) Kametani, T.; Nemoto, H. Tetrahedron 1981, 37, 3-16.
40. Reviews: (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16,10-23. (b) Oppolzer, W. Synthesis 1978, 793-802. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41-61. (d) Kametani, T.; Nemoto, H. Tetrahedron 1981, 37, 3-16.
41. Reviews: (a) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16,10-23. (b) Oppolzer, W. Synthesis 1978, 793-802. (c) Funk, R. L.; Vollhardt, K. P. C. Chem. Soc. Rev. 1980, 9, 41-61. (d) Kametani, T.; Nemoto, H. Tetrahedron 1981, 37, 3-16.
42. e.g. (a) Charlton, J. L.; Bogucki, D.; Guo, P. Can. J. Chem. 1995, 73, 1463-1467. (b) Bogucki, D. E.; Charlton, J. L. J. Org. Chem. 1995, 60, 588-593. (c) Nemoto, H.; Satoh, A.; Fukumoto, K.; Kabuto, C. J. Org. Chem. 1995, 60, 594-600.
43. e.g. (a) Charlton, J. L.; Bogucki, D.; Guo, P. Can. J. Chem. 1995, 73, 1463-1467. (b) Bogucki, D. E.; Charlton, J. L. J. Org. Chem. 1995, 60, 588-593. (c) Nemoto, H.; Satoh, A.; Fukumoto, K.; Kabuto, C. J. Org. Chem. 1995, 60, 594-600.
44. e.g. (a) Charlton, J. L.; Bogucki, D.; Guo, P. Can. J. Chem. 1995, 73, 1463-1467. (b) Bogucki, D. E.; Charlton, J. L. J. Org. Chem. 1995, 60, 588-593. (c) Nemoto, H.; Satoh, A.; Fukumoto, K.; Kabuto, C. J. Org. Chem. 1995, 60, 594-600.
45. (a) Kambe, N.; Tsukamoto, T.; Miyoshi, N.; Murai, S.; Sonoda, N. Bull. Chem. Soc. Jpn. 1986, 59, 3013-3018.
46. (b) Sano, H.; Ohtsuka, H.; Migita, T. J. Am. Chem. Soc. 1988, 110, 2014-2015.
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48. (d) Fujihara, H.; Yabe, M.; Furukawa, N. J. Org. Chem. 1993, 58, 5291-5292.
49. (e) Sato, H.; Isono, N.; Okamura, K.; Date, T.; Mori, M. Tetrahedron Lett. 1994, 35, 2035-2038; and see references cited therein.
50. Preliminary results with a KrF excimer laser: Ouchi, A.; Koga, Y. Chem. Commun. 1996, 2075-2076.
51. Original data are given as Supporting Information.
52. The stereoisomer 5b obtained from 4c in Table 1 of ref 13 was found to be a different compound.
53. Jaffé, H. H.; Orchin, M. Theory and Application of Ultraviolet Spectroscopy; John Wiley & Sons: New York, 1962; Chapter 12, section 12.2.
54. Reference 16; Chapter 17, section 17.2.
55. -1 and 269 nm for anisole: ref 16; Table 12.4.
56. -1 and 254 nm: ref 16; Table 17.1.
57. max at ca. 320 nm, corresponding to open-form monoradical 2A, and broad absorption in the range 430-500 nm, corresponding to bridged-form monoradical 2B and PhX radical.
58. e.g. Tokumura, K.; Udagawa, M.; Ozaki, T.; Itoh, M. Chem. Phys. Lett. 1987, 141, 558-563.
59. Calculated by using PM3 method (RHF, CI) in the MOPAC version 6.0: cf. Stewart, J. J. P. QCPE Bull. 1989, 9, 10.
60. The bridged-form of the monoradical generated from 1,8-bis(substituted-methyl)naphthalene (substituent: SPh, SePh) showed broad absorption at 400-520 nm, whereas the absorption of the open-form monoradical was observed at 330-380 nm: Ouchi, A.; Koga, Y.; Alam, M. M.; Ito, O. J. Chem. Soc., Perkin Trans. 2 1996, 1705-1709.
61. Baff, L. The chemistry of organic selenium and tellurium compounds; Patai, S., Rappoport, Z., Ed.; Wiley: Chichester, 1986; vol. 1, chapter 4, p 159.
62. Wintgens, V.; Netto-Ferreira, J. C.; Casal, H. L.; Scaiano, J. C. J. Am. Chem. Soc. 1990, 112, 2363-2367.