Ring expansion of diazo-functionalized 4-hydroxycyclobutenone: Catalytic ring opening and recyclization to 2(5H)-furanone/cyclopentenedione and thermal 4π-8π electrocyclic ring opening-closure to diazepinedione

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 707-712

  Ohno, Masatomi ^a   Noda, Masashi ^a   Yamamoto, Yoshihiko ^a   Eguchi, Shoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENE DERIVATIVE; DIAZEPINE DERIVATIVE; FURANONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECOMPOSITION; ORGANIC CHEMISTRY; PHOTOLYSIS; STRUCTURE ANALYSIS;

EID: 0033524882     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980523d     Document Type: Article

References (42)

1. (a) Schmidt, A. H. Synthesis 1980, 961.
2. (b) Liebeskind, L. S. Tetrahedron 1989, 45, 3053.
3. (c) Moore, H. W.; Yerxa, B. R. Chemtracts Org. Chem. 1992, 5, 273.
4. (d) Ohno, M.; Yamamoto, Y.; Eguchi, S. J. Synth. Org. Chem., Jpn. 1997, 55, 785.
5. For a theoretical study, see (a) Niwayama, S.; Kallel, E. A.; Sheu, C.; Houk, K. N. J. Org. Chem. 1996, 61, 2517. (b) Niwayama, S.; Kallel, E. A.; Spellmeyer, D. C.; Sheu, C.; Houk, K. N. J. Org. Chem. 1996, 61, 2813.
6. For a theoretical study, see (a) Niwayama, S.; Kallel, E. A.; Sheu, C.; Houk, K. N. J. Org. Chem. 1996, 61, 2517. (b) Niwayama, S.; Kallel, E. A.; Spellmeyer, D. C.; Sheu, C.; Houk, K. N. J. Org. Chem. 1996, 61, 2813.
7. For recent examples, see: (a) Sun, L.; Liebeskind, L. S. J. Org. Chem. 1995, 60, 8194. (b) Xiong, Y.; Xia, H.; Moore, H. W. J. Org. Chem. 1995, 60, 6460. (c) Xiong, Y.; Moore, H. W. J. Org. Chem. 1996, 61, 9168. (d) Tomooka, C. S.; Liu, H.; Moore, H. W. J. Org. Chem. 1996, 61, 6009. (e) Sun, L.; Liebeskind, L. S. Tetrahedron Lett. 1997, 38, 3663. (f) Onofrey, T. J.; Gomez, D.; Winters, M.; Moore, H. W. J. Org. Chem. 1997, 62, 5658.
8. For recent examples, see: (a) Sun, L.; Liebeskind, L. S. J. Org. Chem. 1995, 60, 8194. (b) Xiong, Y.; Xia, H.; Moore, H. W. J. Org. Chem. 1995, 60, 6460. (c) Xiong, Y.; Moore, H. W. J. Org. Chem. 1996, 61, 9168. (d) Tomooka, C. S.; Liu, H.; Moore, H. W. J. Org. Chem. 1996, 61, 6009. (e) Sun, L.; Liebeskind, L. S. Tetrahedron Lett. 1997, 38, 3663. (f) Onofrey, T. J.; Gomez, D.; Winters, M.; Moore, H. W. J. Org. Chem. 1997, 62, 5658.
9. For recent examples, see: (a) Sun, L.; Liebeskind, L. S. J. Org. Chem. 1995, 60, 8194. (b) Xiong, Y.; Xia, H.; Moore, H. W. J. Org. Chem. 1995, 60, 6460. (c) Xiong, Y.; Moore, H. W. J. Org. Chem. 1996, 61, 9168. (d) Tomooka, C. S.; Liu, H.; Moore, H. W. J. Org. Chem. 1996, 61, 6009. (e) Sun, L.; Liebeskind, L. S. Tetrahedron Lett. 1997, 38, 3663. (f) Onofrey, T. J.; Gomez, D.; Winters, M.; Moore, H. W. J. Org. Chem. 1997, 62, 5658.
10. For recent examples, see: (a) Sun, L.; Liebeskind, L. S. J. Org. Chem. 1995, 60, 8194. (b) Xiong, Y.; Xia, H.; Moore, H. W. J. Org. Chem. 1995, 60, 6460. (c) Xiong, Y.; Moore, H. W. J. Org. Chem. 1996, 61, 9168. (d) Tomooka, C. S.; Liu, H.; Moore, H. W. J. Org. Chem. 1996, 61, 6009. (e) Sun, L.; Liebeskind, L. S. Tetrahedron Lett. 1997, 38, 3663. (f) Onofrey, T. J.; Gomez, D.; Winters, M.; Moore, H. W. J. Org. Chem. 1997, 62, 5658.
11. For recent examples, see: (a) Sun, L.; Liebeskind, L. S. J. Org. Chem. 1995, 60, 8194. (b) Xiong, Y.; Xia, H.; Moore, H. W. J. Org. Chem. 1995, 60, 6460. (c) Xiong, Y.; Moore, H. W. J. Org. Chem. 1996, 61, 9168. (d) Tomooka, C. S.; Liu, H.; Moore, H. W. J. Org. Chem. 1996, 61, 6009. (e) Sun, L.; Liebeskind, L. S. Tetrahedron Lett. 1997, 38, 3663. (f) Onofrey, T. J.; Gomez, D.; Winters, M.; Moore, H. W. J. Org. Chem. 1997, 62, 5658.
12. For recent examples, see: (a) Sun, L.; Liebeskind, L. S. J. Org. Chem. 1995, 60, 8194. (b) Xiong, Y.; Xia, H.; Moore, H. W. J. Org. Chem. 1995, 60, 6460. (c) Xiong, Y.; Moore, H. W. J. Org. Chem. 1996, 61, 9168. (d) Tomooka, C. S.; Liu, H.; Moore, H. W. J. Org. Chem. 1996, 61, 6009. (e) Sun, L.; Liebeskind, L. S. Tetrahedron Lett. 1997, 38, 3663. (f) Onofrey, T. J.; Gomez, D.; Winters, M.; Moore, H. W. J. Org. Chem. 1997, 62, 5658.
13. Paquette, L. A.; Kuo, L. H.; Doyon, J. J. Am. Chem. Soc. 1997, 119, 3038 and refs cited therein.
14. (a) Sun, L.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 6856.
15. (b) Yamamoto, Y.; Ohno, M.; Eguchi, S. Tetrahedron Lett. 1995, 31, 5539.
16. (c) Yamamoto, Y.; Ohno, M.; Eguchi, S. J. Am. Chem. Soc. 1995, 117, 9653.
17. (d) Paquette, L. A.; Sturino, C. F.; Dousso, P. J. Am. Chem. Soc. 1996, 118, 9456.
18. (e) Yamamoto, Y.; Ohno, M.; Eguchi, S. J. Org. Chem. 1996, 61, 9246.
19. (f) Yamamoto, Y.; Noda, M.; Ohno, M.; Eguchi, S. J. Org. Chem. 1997, 62, 1292.
20. (a) Liebeskind, L. S.; Chidambaram, R. J. Am. Chem. Soc. 1987, 709, 5025.
21. (b) Liebeskind, L. S.; Mitchell, D.; Foster, B. S. J. Am. Chem. Soc. 1987, 109, 7908.
22. (c) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291.
23. (d) Zora, M.; Herndon, J. W. J. Org. Chem. 1994, 59, 699.
24. (e) Liebeskind, L. S.; Bombrun, A. J. Org. Chem. 1994, 59, 1149.
25. Squarate 2 was not suitable since the nucleophilic addition did not occur at -78°C. Furthermore, α-diazo carbonyl compounds were used since derivatives of diazoalkane such as (trimethylsilyl)diazomethane were too unstable [decomposition during workup gave only 12% of the cyclopentenedione (13: R = TMS) as a product].
26. Pellicciari, R.; Natalini, B.; Sadeghpour, B. M.; Marinozzi, M.; Snyder, J. P.; Williamson, B. L.; Kuethe, J. T.; Padwa, A. J. Am. Chem. Soc. 1996, 118, 1. References are listed for some reactions of α-diazo β-hydroxy carbonyl compounds.
27. Begley, M. L.; Gedge, D. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1978, 60.
28. Base-promoted conversion of 5-acylidene-2(5H)-furanone to 2-acyl-4-cyclopentene-1,3-dione has been reported: Gedge, D. R.; Pattenden, G. J. Chem. Soc., Chem. Commun. 1978, 880.
29. Control experiments suggested that the acid-catalyzed conditions had little effect on the geometrical isomerization of formed furanones 14.
30. Shimada, J.; Hashimoto, K.; Kim, B. H.; Nakamura, E.; Kuwajima, I. J. Am. Chem. Soc. 1984, 106, 1759.
31. Ohno, M.; Itoh, M.; Umeda, M.; Furuta, R.; Kondo, K.; Eguchi, S. J. Am. Chem. Soc. 1996, 118, 7075. See ref 6d for the case of chromium carbene complexes.
32. The rearrangement of cyclobutylcarbene to cyclopentene has been reported: Paskovich, D. H.; Kwok, P. W. N. Tetrahedron Lett. 1967, 2227. For a general discussion on 1,2-rearrangement of carbene, see Nickon, A. Acc. Chem. Res. 1993, 26, 84, and refs cited therein.
33. The rearrangement of cyclobutylcarbene to cyclopentene has been reported: Paskovich, D. H.; Kwok, P. W. N. Tetrahedron Lett. 1967, 2227. For a general discussion on 1,2-rearrangement of carbene, see Nickon, A. Acc. Chem. Res. 1993, 26, 84, and refs cited therein.
34. 4; see ref 13.
35. Zwitterionic intermediates have often been proposed in the Rh-promoted carbene rearrangement, in which a metallacycle is postulated as a plausible intermediate: (a) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (b) Müller, P.; Pautex, N.; Doyle, A. P.; Bagheri, V. Helv. Chim. Acta 1990, 73, 1233.
36. Zwitterionic intermediates have often been proposed in the Rh- promoted carbene rearrangement, in which a metallacycle is postulated as a plausible intermediate: (a) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (b) Müller, P.; Pautex, N.; Doyle, A. P.; Bagheri, V. Helv. Chim. Acta 1990, 73, 1233.
37. In an exception, the (Z)-isomer was a minor product in the Rh-catalysis of 12a (entry 6), probably because of coordination with a Rh center.
38. (a) Sharp, J. T. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 7, pp 595-604.
39. (b) For an example of 6π electrocyclization of diazoketene, see Tomioka, H.; Okuno, A.; Sugiyama, T.; Murata, S. J. Org. Chem. 1995, 60, 2344.
40. For a previous ring transformation based on 1 to a seven-membered ring, see: Huffman, M. A.; Liebeskind, L. S. J. Am. Chem. Soc. 1993, 115, 4895.
41. For the synthesis of these types of compounds from 1, see (a) Reed, M. W.; Polart, D. J.; Perri, S. T.; Foland, L. D.; Moore, H. W. J. Org. Chem. 1988, 53, 2477. (b) Liebeskind, L. S.; Fengl, R. W.; Wirtz, K R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482.
42. For the synthesis of these types of compounds from 1, see (a) Reed, M. W.; Polart, D. J.; Perri, S. T.; Foland, L. D.; Moore, H. W. J. Org. Chem. 1988, 53, 2477. (b) Liebeskind, L. S.; Fengl, R. W.; Wirtz, K R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482.