Kishner's reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran, a highly reactive ene in the ene reaction

Journal of Organic Chemistry

Volumn 70, Issue 7, 2005, Pages 2862-2865

  Miles, William H ^a   Dethoff, Elizabeth A ^a   Tuson, Hannah H ^a   Ulas, Gözde ^a  

^a LAFAYETTE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALDEHYDES; AROMATIC COMPOUNDS; COMPLEXATION; REACTION KINETICS; REDUCTION;

CARBONYL-ENE REACTIONS; ELECTRON DONOR ACCEPTOR COMPLEX; KISHNER'S REDUCTION; REDUCTION PRODUCTS;

KETONES;

1,4 BENZOQUINONE; 1,4 HYDROQUINONE; 2 FURYLHYDRAZONE; 2 METHYLENE 2,3 DIHYDROFURAN; 2,2' DIHYDROXY 1,1' BINAPHTHYL; ALCOHOL; ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; FURAN DERIVATIVE; HYDRAZONE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ELECTRON; REDUCTION;

EID: 17044418097     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0479112     Document Type: Article

References (40)

1. Todd, D. Org. React. 1948, 4, 378-422.
2. Wood, J. L.; Porco, J. A., Jr.; Taunton, J.; Lee, A. Y.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 5898-5900.
3. Taber, D. F.; Stachel, S. J. Tetrahedron Lett. 1992, 33, 903-906.
4. Milder methods for generating a benzylic diazene has led to the synthesis of alicyclic isomers of aromatic compounds. See: Myers, A. G.; Movassaghi, M.; Zheng, B. J. Am. Chem. Soc. 1997, 119, 8572-8573.
5. (a) Kishner, N. Zh. Obs. Khim. 1931, 1, 1212-1228; Chem. Abstr. 1931, 26, 51393.
6. (a) Kishner, N. Zh. Obs. Khim. 1931, 1, 1212-1228; Chem. Abstr. 1931, 26, 51393.
7. (b) Kishner, N. Zh. Obs. Khim. 1933, 3, 198-200; Chem. Abstr. 1933, 28, 14046.
8. (b) Kishner, N. Zh. Obs. Khim. 1933, 3, 198-200; Chem. Abstr. 1933, 28, 14046.
9. Miles, W. H.; Berreth, C. L.; Smiley, P. M. Tetrahedron Lett. 1993, 34, 5221-5222.
10. Rice, H. L. J. Am. Chem. Soc. 1952, 74, 3193-3194.
11. Miles, W. H.; Berreth, C. L.; Anderton, C. A. Tetrahedron Lett. 1996, 37, 7893-7896. Miles, W. H.; Fialcowitz, E. J.; Halstead, E. S. Tetrahedron 2001, 57, 9925-9929. Miles, W. H.; Connell, K. B. Tetrahedron Lett. 2003, 44, 1161-1163.
12. Miles, W. H.; Berreth, C. L.; Anderton, C. A. Tetrahedron Lett. 1996, 37, 7893-7896. Miles, W. H.; Fialcowitz, E. J.; Halstead, E. S. Tetrahedron 2001, 57, 9925-9929. Miles, W. H.; Connell, K. B. Tetrahedron Lett. 2003, 44, 1161-1163.
13. Miles, W. H.; Berreth, C. L.; Anderton, C. A. Tetrahedron Lett. 1996, 37, 7893-7896. Miles, W. H.; Fialcowitz, E. J.; Halstead, E. S. Tetrahedron 2001, 57, 9925-9929. Miles, W. H.; Connell, K. B. Tetrahedron Lett. 2003, 44, 1161-1163.
14. For reviews, see: Dias, L. C. Curr. Org. Chem. 2000, 4, 305-342. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050.
15. For reviews, see: Dias, L. C. Curr. Org. Chem. 2000, 4, 305-342. Mikami, K.; Shimizu, M. Chem. Rev. 1992, 92, 1021-1050.
16. For recent advances, see: Alcaide, B.; Almendros, P.; Pardo, C.; Rodríguez-Ranera, C.; Rodríguez-Vicente J. Org. Chem. 2003, 68, 3106-3111. Williams, J. T.; Bahia, P. S.; Snaith, J. S. Org. Lett. 2002, 4, 3727-3730. Okachi, T.; Fujimoto, K.; Onaka, M. Org. Lett. 2002, 4, 1667-1669.
17. For recent advances, see: Alcaide, B.; Almendros, P.; Pardo, C.; Rodríguez-Ranera, C.; Rodríguez-Vicente J. Org. Chem. 2003, 68, 3106-3111. Williams, J. T.; Bahia, P. S.; Snaith, J. S. Org. Lett. 2002, 4, 3727-3730. Okachi, T.; Fujimoto, K.; Onaka, M. Org. Lett. 2002, 4, 1667-1669.
18. For recent advances, see: Alcaide, B.; Almendros, P.; Pardo, C.; Rodríguez-Ranera, C.; Rodríguez-Vicente J. Org. Chem. 2003, 68, 3106-3111. Williams, J. T.; Bahia, P. S.; Snaith, J. S. Org. Lett. 2002, 4, 3727-3730. Okachi, T.; Fujimoto, K.; Onaka, M. Org. Lett. 2002, 4, 1667-1669.
19. Graham, W. D.; Green, J. G., Pryor, W. A. J. Org. Chem. 1979, 44, 907-914. Gajewski, J. J.; Gortva, A. M. J. Am. Chem. Soc. 1982, 104, 334-335. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373-378. Maischein, J.; Vilsmaier, E. Liebigs Ann. Chem. 1988, 371-375. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 4685-4686. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585-2588. Ferraris, D.; Young, B.; Cox, C.; Duddling, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67-77.
20. Graham, W. D.; Green, J. G., Pryor, W. A. J. Org. Chem. 1979, 44, 907-914. Gajewski, J. J.; Gortva, A. M. J. Am. Chem. Soc. 1982, 104, 334-335. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373-378. Maischein, J.; Vilsmaier, E. Liebigs Ann. Chem. 1988, 371-375. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 4685-4686. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585-2588. Ferraris, D.; Young, B.; Cox, C.; Duddling, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67-77.
21. Graham, W. D.; Green, J. G., Pryor, W. A. J. Org. Chem. 1979, 44, 907-914. Gajewski, J. J.; Gortva, A. M. J. Am. Chem. Soc. 1982, 104, 334-335. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373-378. Maischein, J.; Vilsmaier, E. Liebigs Ann. Chem. 1988, 371-375. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 4685-4686. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585-2588. Ferraris, D.; Young, B.; Cox, C.; Duddling, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67-77.
22. Graham, W. D.; Green, J. G., Pryor, W. A. J. Org. Chem. 1979, 44, 907-914. Gajewski, J. J.; Gortva, A. M. J. Am. Chem. Soc. 1982, 104, 334-335. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373-378. Maischein, J.; Vilsmaier, E. Liebigs Ann. Chem. 1988, 371-375. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 4685-4686. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585-2588. Ferraris, D.; Young, B.; Cox, C.; Duddling, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67-77.
23. Graham, W. D.; Green, J. G., Pryor, W. A. J. Org. Chem. 1979, 44, 907-914. Gajewski, J. J.; Gortva, A. M. J. Am. Chem. Soc. 1982, 104, 334-335. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373-378. Maischein, J.; Vilsmaier, E. Liebigs Ann. Chem. 1988, 371-375. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 4685-4686. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585-2588. Ferraris, D.; Young, B.; Cox, C.; Duddling, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67-77.
24. Graham, W. D.; Green, J. G., Pryor, W. A. J. Org. Chem. 1979, 44, 907-914. Gajewski, J. J.; Gortva, A. M. J. Am. Chem. Soc. 1982, 104, 334-335. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373-378. Maischein, J.; Vilsmaier, E. Liebigs Ann. Chem. 1988, 371-375. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 4685-4686. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585-2588. Ferraris, D.; Young, B.; Cox, C.; Duddling, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67-77.
25. Graham, W. D.; Green, J. G., Pryor, W. A. J. Org. Chem. 1979, 44, 907-914. Gajewski, J. J.; Gortva, A. M. J. Am. Chem. Soc. 1982, 104, 334-335. Gajewski, J. J.; Gortva, A. M. J. Org. Chem. 1989, 54, 373-378. Maischein, J.; Vilsmaier, E. Liebigs Ann. Chem. 1988, 371-375. Tidwell, J. H.; Senn, D. R.; Buchwald, S. L. J. Am. Chem. Soc. 1991, 113, 4685-4686. Ojida, A.; Abe, A.; Kanematsu, K. Heterocycles 1994, 38, 2585-2588. Ferraris, D.; Young, B.; Cox, C.; Duddling, T.; Drury, W. J., III; Ryzhkov, L.; Taggi, A. E.; Lectka, T. J. Am. Chem. Soc. 2002, 124, 67-77.
26. For leading references on asymmetric Ti(IV)/BINOL-catalyzed reactions, see: Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954. Costa, A. L.; Piazza, M. G.; Tagiavini, E.; Trombini, C.; Uman-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001-7002. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468.
27. For leading references on asymmetric Ti(IV)/BINOL-catalyzed reactions, see: Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954. Costa, A. L.; Piazza, M. G.; Tagiavini, E.; Trombini, C.; Uman-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001-7002. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468.
28. For leading references on asymmetric Ti(IV)/BINOL-catalyzed reactions, see: Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949-3954. Costa, A. L.; Piazza, M. G.; Tagiavini, E.; Trombini, C.; Uman-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001-7002. Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467-8468.
29. For a review of furan chemistry, see: Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1988, 54, 1955-2020.
30. For recent furan papers, see: Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164-11165. Méndez-Andina, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095-4097. Stauffer, F.; Neier, R. Org. Lett. 2000, 2, 3535-3537.
31. For recent furan papers, see: Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164-11165. Méndez-Andina, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095-4097. Stauffer, F.; Neier, R. Org. Lett. 2000, 2, 3535-3537.
32. For recent furan papers, see: Yao, T.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2004, 126, 11164-11165. Méndez-Andina, J.; Paquette, L. A. Org. Lett. 2000, 2, 4095-4097. Stauffer, F.; Neier, R. Org. Lett. 2000, 2, 3535-3537.
33. For a review, see: Lipshutz, B. H. Chem. Rev. 1986, 86, 795-819.
34. For recent applications, see: Padwa, A.; Brodney, M. A.; Lynch, S. M.; Rashatasakhon, P.; Wang, Q.; Zhang, H. J. Org. Chem. 2004, 69, 3735-3745. Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113-4115. Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Arjona, O.; Menchaca, R.; Plumet, J. Org. Lett. 2001, 3, 107-109.
35. For recent applications, see: Padwa, A.; Brodney, M. A.; Lynch, S. M.; Rashatasakhon, P.; Wang, Q.; Zhang, H. J. Org. Chem. 2004, 69, 3735-3745. Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113-4115. Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Arjona, O.; Menchaca, R.; Plumet, J. Org. Lett. 2001, 3, 107-109.
36. For recent applications, see: Padwa, A.; Brodney, M. A.; Lynch, S. M.; Rashatasakhon, P.; Wang, Q.; Zhang, H. J. Org. Chem. 2004, 69, 3735-3745. Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113-4115. Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Arjona, O.; Menchaca, R.; Plumet, J. Org. Lett. 2001, 3, 107-109.
37. For recent applications, see: Padwa, A.; Brodney, M. A.; Lynch, S. M.; Rashatasakhon, P.; Wang, Q.; Zhang, H. J. Org. Chem. 2004, 69, 3735-3745. Hughes, C. C.; Kennedy-Smith, J. J.; Trauner, D. Org. Lett. 2003, 5, 4113-4115. Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513-3516. Arjona, O.; Menchaca, R.; Plumet, J. Org. Lett. 2001, 3, 107-109.
38. Kabalka, G. W.; Summers, S. T. J. Org. Chem. 1981, 46, 1217-1218.
39. Solladié-Cavallo, A.; Roje, M.; Isarno, T.; Sunjic, V.; Vinkovic, V. Eur. J. Org. Chem. 2000, 1077-1080.
40. Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490-11495.