Stereoselective construction of cyclic ethers via intramolecular acyl radical cyclizations: A practical solution to decarbonylation

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2252-2253

  Evans, P Andrew ^a   Roseman, Jamie D ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXEPANE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029976190     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960175k     Document Type: Article

References (48)

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16. For representative recent examples of cyclic ether synthesis via radical cyclizations see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32, 1491. (e) Rawal, V. H.; Singh, S P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837 and pertinent references within these articles.
17. For representative recent examples of cyclic ether synthesis via radical cyclizations see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32, 1491. (e) Rawal, V. H.; Singh, S P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837 and pertinent references within these articles.
18. For representative recent examples of cyclic ether synthesis via radical cyclizations see: (a) Ueno, Y.; Chino.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564. (b) Stork, G.; Mook, R., Jr.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741. (c) Hutchinson, J. H.; Pattenden, G.; Myers, P. L. Tetrahedron Lett. 1987, 28, 1313. (d) Lolkema, L. D. M.; Hiemstra, H.; Al Ghouch, A. A.; Speckamp, W. N. Tetrahedron Lett. 1991, 32, 1491. (e) Rawal, V. H.; Singh, S P.; Dufour, C.; Michoud, C. J. Org. Chem. 1993, 58, 7718. (f) Burke, S. D.; Jung, W.-J. Tetrahedron Lett. 1994, 35, 5837 and pertinent references within these articles.
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24. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
25. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
26. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
27. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
28. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
29. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
30. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
31. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
32. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
33. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
34. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
35. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
36. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
37. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
38. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
39. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
40. Crich, D.; Fortt, S. M. Tetrahedron Lett. 1987, 28, 2895. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1988, 53, 3377. Crich, D.; Fortt, S. M.; Tetrahedron Lett. 1988, 29, 2585. Crich, D.; Eustace, K. A.; Richie, T. J. Heterocycles 1989, 28, 67. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Chem. Commun, 1989, 1366. Crich, D.; Fortt, S. M. Tetrahedron 1989, 45, 6581. Batty, D.; Crich, D.; Fortt, S. M. J. Chem. Soc., Perkin Trans. 1 1990, 2875. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4003. Boger, D. L.; Mathvink, R. J J. Am. Chem. Soc. 1990, 112, 4008. Boger, D. L.; Mathvink, R. J. J. Org. Chem. 1990, 55, 5442. Astley, M. P.; Pattenden, G. Synthesis 1992, 101, Batty, D.; Crich, D. Tetrahedron Lett. 1992, 33, 875. Boger, D. L.; Mathvink, R. J. J. Org Chem. 1992, 57, 1429. Batty, D.; Crich, D. J. Chem. Soc., Perkin Trans. 1 1992, 3193. Chen, L.; Gill, B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593 Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271 and pertinent references within these articles. For an example of seleno carbonates, see: Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and pertinent references therein.
41. Evans, P. A.; Roseman, J. D. Tetrahedron Lett. 1995, 36, 31.
42. Beckwith, A. L. J.; Easton, C. J.; Lawrence, T.; Serelis, A. K. Aust. J. Chem. 1983, 36, 545.
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45. Rtu, I.; Hasegawa, M.; Kurihara, A.; Ogawa, A.; Tsunoi, S.; Sonoda, N. Synlett 1993, 143 and pertinent references therein.
46. For an investigation on the relationship between temperature and the rate of decarbonylation of acyl radicals, see: Pfenninger, J.; Heuberger, C.; Graf, W. Helv. Chim. Acta 1980, 63, 2328.
47. The acyl selenides were prepared from the corresponding carboxylic acids, see Batty, D.; Crich, D. Synthesis 1990, 273.
48. The LUMO of an acrylate and a vinyl ether is known to have larger coefficients at the β- and α-carbon, respectively, thus reinforcing each other in a β-alkoxyacrylate See: Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley and Sons: New York, 1977; p 186.