Photochemical reactions of alkoxy-containing-alkyl phenylglyoxylates: Remote hydrogen abstraction

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 9, 1997, Pages 1751-1754

  Hu, Shengkui ^a   Neckers, D C ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011207177     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700948h     Document Type: Article

References (22)

1. (a) E. S. Huyser and D. C. Neckers, J. Org. Chem., 1964, 29, 276;
2. (b) S. Hu and D. C. Neckers, J. Org. Chem., 1996, 61, 6407 and references therein.
3. For Norrish Type II reactions, see ref. 1 and (a) R. J. Tepper and M. C. Pirrung, J. Org. Chem., 1995, 60, 2461. For photocyclo- addition, see (b) S. Hu and D. C. Neckers. J. Org. Chem., 1997, 62, 564; H. Buschmann, H.-D. Scharf, N. Hoffmann and P. Esser, Angew. Chem., Int. Ed. Engl., 1991, 30, 477; H. Buschmann, H.-D. Scharf, N. Hoffmann, M. W. Plath and J. Runsink, J. Am. Chem Soc., 1989, 111, 5367. For electron transfer reaction, see (e) S. Hu and D. C. Neckers, Tetrahedron, 1997, 53, 2751; (f) S. Hu and D. C. Neckers, J. Org. Chem., in the press. For intermolecular hydrogen abstraction, see ref. 1(b), and; (g) A. Schönberg, N. Latif, R. Moubasher and A. Sina, J. Chem. Soc., 1951, 1364.
4. For Norrish Type II reactions, see ref. 1 and (a) R. J. Tepper and M. C. Pirrung, J. Org. Chem., 1995, 60, 2461. For photocyclo-addition, see (b) S. Hu and D. C. Neckers. J. Org. Chem., 1997, 62, 564; H. Buschmann, H.-D. Scharf, N. Hoffmann and P. Esser, Angew. Chem., Int. Ed. Engl., 1991, 30, 477; H. Buschmann, H.-D. Scharf, N. Hoffmann, M. W. Plath and J. Runsink, J. Am. Chem Soc., 1989, 111, 5367. For electron transfer reaction, see (e) S. Hu and D. C. Neckers, Tetrahedron, 1997, 53, 2751; (f) S. Hu and D. C. Neckers, J. Org. Chem., in the press. For intermolecular hydrogen abstraction, see ref. 1(b), and; (g) A. Schönberg, N. Latif, R. Moubasher and A. Sina, J. Chem. Soc., 1951, 1364.
5. For Norrish Type II reactions, see ref. 1 and (a) R. J. Tepper and M. C. Pirrung, J. Org. Chem., 1995, 60, 2461. For photocyclo- addition, see (b) S. Hu and D. C. Neckers. J. Org. Chem., 1997, 62, 564; H. Buschmann, H.-D. Scharf, N. Hoffmann and P. Esser, Angew. Chem., Int. Ed. Engl., 1991, 30, 477; H. Buschmann, H.-D. Scharf, N. Hoffmann, M. W. Plath and J. Runsink, J. Am. Chem Soc., 1989, 111, 5367. For electron transfer reaction, see (e) S. Hu and D. C. Neckers, Tetrahedron, 1997, 53, 2751; (f) S. Hu and D. C. Neckers, J. Org. Chem., in the press. For intermolecular hydrogen abstraction, see ref. 1(b), and; (g) A. Schönberg, N. Latif, R. Moubasher and A. Sina, J. Chem. Soc., 1951, 1364.
6. For Norrish Type II reactions, see ref. 1 and (a) R. J. Tepper and M. C. Pirrung, J. Org. Chem., 1995, 60, 2461. For photocyclo- addition, see (b) S. Hu and D. C. Neckers. J. Org. Chem., 1997, 62, 564; H. Buschmann, H.-D. Scharf, N. Hoffmann and P. Esser, Angew. Chem., Int. Ed. Engl., 1991, 30, 477; H. Buschmann, H.-D. Scharf, N. Hoffmann, M. W. Plath and J. Runsink, J. Am. Chem Soc., 1989, 111, 5367. For electron transfer reaction, see (e) S. Hu and D. C. Neckers, Tetrahedron, 1997, 53, 2751; (f) S. Hu and D. C. Neckers, J. Org. Chem., in the press. For intermolecular hydrogen abstraction, see ref. 1(b), and; (g) A. Schönberg, N. Latif, R. Moubasher and A. Sina, J. Chem. Soc., 1951, 1364.
7. For Norrish Type II reactions, see ref. 1 and (a) R. J. Tepper and M. C. Pirrung, J. Org. Chem., 1995, 60, 2461. For photocyclo- addition, see (b) S. Hu and D. C. Neckers. J. Org. Chem., 1997, 62, 564; H. Buschmann, H.-D. Scharf, N. Hoffmann and P. Esser, Angew. Chem., Int. Ed. Engl., 1991, 30, 477; H. Buschmann, H.-D. Scharf, N. Hoffmann, M. W. Plath and J. Runsink, J. Am. Chem Soc., 1989, 111, 5367. For electron transfer reaction, see (e) S. Hu and D. C. Neckers, Tetrahedron, 1997, 53, 2751; (f) S. Hu and D. C. Neckers, J. Org. Chem., in the press. For intermolecular hydrogen abstraction, see ref. 1(b), and; (g) A. Schönberg, N. Latif, R. Moubasher and A. Sina, J. Chem. Soc., 1951, 1364.
8. For Norrish Type II reactions, see ref. 1 and (a) R. J. Tepper and M. C. Pirrung, J. Org. Chem., 1995, 60, 2461. For photocyclo- addition, see (b) S. Hu and D. C. Neckers. J. Org. Chem., 1997, 62, 564; H. Buschmann, H.-D. Scharf, N. Hoffmann and P. Esser, Angew. Chem., Int. Ed. Engl., 1991, 30, 477; H. Buschmann, H.-D. Scharf, N. Hoffmann, M. W. Plath and J. Runsink, J. Am. Chem Soc., 1989, 111, 5367. For electron transfer reaction, see (e) S. Hu and D. C. Neckers, Tetrahedron, 1997, 53, 2751; (f) S. Hu and D. C. Neckers, J. Org. Chem., in the press. For intermolecular hydrogen abstraction, see ref. 1(b), and; (g) A. Schönberg, N. Latif, R. Moubasher and A. Sina, J. Chem. Soc., 1951, 1364.
9. For Norrish Type II reactions, see ref. 1 and (a) R. J. Tepper and M. C. Pirrung, J. Org. Chem., 1995, 60, 2461. For photocyclo- addition, see (b) S. Hu and D. C. Neckers. J. Org. Chem., 1997, 62, 564; H. Buschmann, H.-D. Scharf, N. Hoffmann and P. Esser, Angew. Chem., Int. Ed. Engl., 1991, 30, 477; H. Buschmann, H.-D. Scharf, N. Hoffmann, M. W. Plath and J. Runsink, J. Am. Chem Soc., 1989, 111, 5367. For electron transfer reaction, see (e) S. Hu and D. C. Neckers, Tetrahedron, 1997, 53, 2751; (f) S. Hu and D. C. Neckers, J. Org. Chem., in the press. For intermolecular hydrogen abstraction, see ref. 1(b), and; (g) A. Schönberg, N. Latif, R. Moubasher and A. Sina, J. Chem. Soc., 1951, 1364.
10. For oxidizing alcohols to aldehydes and ketones, see (a) R. W. Binkley, J. Org. Chem., 1976, 41, 3030; (b) H. A. J. Carless and G. K. Fekarabobo, Tetrahedron Lett., 1983, 24, 107. For synthesis of β-lactams. see (c) H. Aoyama, M. Sakamoto, K. Yoshida and Y. Omote, J. Heterocycl. Chem., 1983, 20, 1099. For uses in photoresists, see (d) S. Hu, A. Mejiritski and D. C. Neckers, Chem. Mater., submitted.
11. For oxidizing alcohols to aldehydes and ketones, see (a) R. W. Binkley, J. Org. Chem., 1976, 41, 3030; (b) H. A. J. Carless and G. K. Fekarabobo, Tetrahedron Lett., 1983, 24, 107. For synthesis of β-lactams. see (c) H. Aoyama, M. Sakamoto, K. Yoshida and Y. Omote, J. Heterocycl. Chem., 1983, 20, 1099. For uses in photoresists, see (d) S. Hu, A. Mejiritski and D. C. Neckers, Chem. Mater., submitted.
12. For oxidizing alcohols to aldehydes and ketones, see (a) R. W. Binkley, J. Org. Chem., 1976, 41, 3030; (b) H. A. J. Carless and G. K. Fekarabobo, Tetrahedron Lett., 1983, 24, 107. For synthesis of β-lactams. see (c) H. Aoyama, M. Sakamoto, K. Yoshida and Y. Omote, J. Heterocycl. Chem., 1983, 20, 1099. For uses in photoresists, see (d) S. Hu, A. Mejiritski and D. C. Neckers, Chem. Mater., submitted.
13. For oxidizing alcohols to aldehydes and ketones, see (a) R. W. Binkley, J. Org. Chem., 1976, 41, 3030; (b) H. A. J. Carless and G. K. Fekarabobo, Tetrahedron Lett., 1983, 24, 107. For synthesis of β-lactams. see (c) H. Aoyama, M. Sakamoto, K. Yoshida and Y. Omote, J. Heterocycl. Chem., 1983, 20, 1099. For uses in photoresists, see (d) S. Hu, A. Mejiritski and D. C. Neckers, Chem. Mater., submitted.
14. J. Runsink, H. Koch, A. Nehrings, H.-D. Scharf, E. Nowack and T. Hahn, J. Chem. Soc., Perkin Trans. 2, 1988, 49.
15. (a) S. P. Pappas, B. C. Pappas and J. E. Blackwell, Jr., J. Org. Chem., 1967, 32, 3066;
16. (b) S. P. Pappas, J. E. Alexander and R. D. Zehr, Jr., J. Am. Chem. Soc., 1970, 92, 6927.
17. (a) G. A. Kraus and Y. Wu, J. Am. Chem. Soc., 1992, 114, 8705;
18. (b) G. A. Kraus, W. Zhang and Y. Wu, Chem. Commun., 1996, 2439.
19. For evidence of transannular bonding interaction between two heteroatoms, see T. Fujii, O. Takahashi and N. Furukawa, J. Org. Chem., 1996, 61, 6233 and references therein.
20. P. J. Wagner and A. E. Kemppainen, J. Am. Chem. Soc., 1972, 94, 7495.
21. M. W. Encinas, E. A. Lissi, A. Zanocco, L. C. Stewart and J. C. Scaiano, Can. J. Chem., 1984, 62, 386.
22. W. E. Ford and M. A. J. Rodgers, J. Phys. Chem., 1994, 98, 3822.