Aza-enyne allenes: Thermal reaction behavior of 2,4,5-hexatrienenitriles

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 839-840

  Gillmann, Thomas ^a   Heckhoff, Stefan ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TEMPERATURE;

EID: 0030047062     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02274-0     Document Type: Article

References (22)

1. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. 1991, 103, 1453-1481; Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416.
2. Nicolaou, K. C.; Dai, W.-M. Angew. Chem. 1991, 103, 1453-1481; Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416.
3. (a) Myers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057-8059.
4. (b) Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1989, 111, 9130-9132.
5. (c) Myers, A. G.; Dragovich, P. S.; Kuo, E. Y. J. Am. Chem. Soc. 1992, 114, 9369-9386.
6. (a) Wang, Z.; Wang, K. K. J. Org. Chem. 1994, 59, 4738-4742 and refs cited therein.
7. (b) Grissom, J. W.; Huang, D. J. Org. Chem. 1994, 59, 5114-5116 and refs cited therein.
8. (a) Review: Moore, H. W.; Yerxa, B. R. Chemtracts, Org. Chem. 1992, 5, 273-313.
9. (b) Padwa, A.; Austin, D. J.; Chiacchio, U.; Kassir, J. M.; Rescifina, A.; Xu, S. L. Tetrahedron Lett. 1991, 32, 5923-5926.
10. (c) Saito, I.; Nakatani, K.; Isoe, S.; Maekawa, S. Tetrahedron Lett. 1994, 35, 605-608.
11. For an unsuccessful attempt to cyclize an aza-enyne ketene, see: Yamamoto, Y.; Nunokawa, K.; Ohno, M.; Eguchi, S. Synlett 1993, 781-783.
12. 3 (2.0 mL) and powdered NaOH (1.5 equiv.) was added with stirring for 14 h. Silica was then added and the solvent removed in vacuo. The residue was subjected to flash chromatography (hexane/ethyl acetate 92.5/7.5) to afford pure 1a (0.091 g, 88%).
13. Nicolaou, K. C.; Maligres, P.; Shin, J.; de Leon, E.; Rideout, D. J. Am. Chem. Soc. 1990, 112, 7825-7826.
14. Nicolaou, K. C.; Dai, W.-M.; Hong, Y. P.; Tsay, S.-C; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1993, 115, 7944-7953.
15. +) m/z 269.1416, found 269.1436.
16. To our knowledge, a cyclization of a stabilized radical onto a nitrile function has not been reported previously. Nitriles as radical acceptors are sometimes problematic. For unsuccessful or low yield attempts of ε-cyano radical cyclizations, see: (a) Chenera, B.; Chuang, C.-P.; Hart, D. J.; Hsu, L.-Y. J. Org. Chem. 1985, 50, 5409-5410. (b) Yeung, B.-W. A.; Contelles, J. L. M.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1989, 1160-1162. Knapp, S. Gibson, F. S.; Choe, Y. H. Tetrahedron Lett. 1990, 31, 5397-5400. For successful examples, see: (d) Shono, T.; Kise, N. Tetrahedron Lett. 1990, 31, 1303-1306. (e) Snider, B. B.; Buckman, B. O. J. Org. Chem. 1992, 57, 322-326. (f) Alonso, R. A.; Burgey, C. S.; Rao, B. V.; Vite, G. D.; Vollerthun, R.; Zottola, M. A.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 6666-6672.
17. To our knowledge, a cyclization of a stabilized radical onto a nitrile function has not been reported previously. Nitriles as radical acceptors are sometimes problematic. For unsuccessful or low yield attempts of ε-cyano radical cyclizations, see: (a) Chenera, B.; Chuang, C.-P.; Hart, D. J.; Hsu, L.-Y. J. Org. Chem. 1985, 50, 5409-5410. (b) Yeung, B.-W. A.; Contelles, J. L. M.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1989, 1160-1162. Knapp, S. Gibson, F. S.; Choe, Y. H. Tetrahedron Lett. 1990, 31, 5397-5400. For successful examples, see: (d) Shono, T.; Kise, N. Tetrahedron Lett. 1990, 31, 1303-1306. (e) Snider, B. B.; Buckman, B. O. J. Org. Chem. 1992, 57, 322-326. (f) Alonso, R. A.; Burgey, C. S.; Rao, B. V.; Vite, G. D.; Vollerthun, R.; Zottola, M. A.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 6666-6672.
18. To our knowledge, a cyclization of a stabilized radical onto a nitrile function has not been reported previously. Nitriles as radical acceptors are sometimes problematic. For unsuccessful or low yield attempts of ε-cyano radical cyclizations, see: (a) Chenera, B.; Chuang, C.-P.; Hart, D. J.; Hsu, L.-Y. J. Org. Chem. 1985, 50, 5409-5410. (b) Yeung, B.-W. A.; Contelles, J. L. M.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1989, 1160-1162. Knapp, S. Gibson, F. S.; Choe, Y. H. Tetrahedron Lett. 1990, 31, 5397-5400. For successful examples, see: (d) Shono, T.; Kise, N. Tetrahedron Lett. 1990, 31, 1303-1306. (e) Snider, B. B.; Buckman, B. O. J. Org. Chem. 1992, 57, 322-326. (f) Alonso, R. A.; Burgey, C. S.; Rao, B. V.; Vite, G. D.; Vollerthun, R.; Zottola, M. A.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 6666-6672.
19. To our knowledge, a cyclization of a stabilized radical onto a nitrile function has not been reported previously. Nitriles as radical acceptors are sometimes problematic. For unsuccessful or low yield attempts of ε-cyano radical cyclizations, see: (a) Chenera, B.; Chuang, C.-P.; Hart, D. J.; Hsu, L.-Y. J. Org. Chem. 1985, 50, 5409-5410. (b) Yeung, B.-W. A.; Contelles, J. L. M.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1989, 1160-1162. Knapp, S. Gibson, F. S.; Choe, Y. H. Tetrahedron Lett. 1990, 31, 5397-5400. For successful examples, see: (d) Shono, T.; Kise, N. Tetrahedron Lett. 1990, 31, 1303-1306. (e) Snider, B. B.; Buckman, B. O. J. Org. Chem. 1992, 57, 322-326. (f) Alonso, R. A.; Burgey, C. S.; Rao, B. V.; Vite, G. D.; Vollerthun, R.; Zottola, M. A.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 6666-6672.
20. To our knowledge, a cyclization of a stabilized radical onto a nitrile function has not been reported previously. Nitriles as radical acceptors are sometimes problematic. For unsuccessful or low yield attempts of ε-cyano radical cyclizations, see: (a) Chenera, B.; Chuang, C.-P.; Hart, D. J.; Hsu, L.-Y. J. Org. Chem. 1985, 50, 5409-5410. (b) Yeung, B.-W. A.; Contelles, J. L. M.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1989, 1160-1162. Knapp, S. Gibson, F. S.; Choe, Y. H. Tetrahedron Lett. 1990, 31, 5397-5400. For successful examples, see: (d) Shono, T.; Kise, N. Tetrahedron Lett. 1990, 31, 1303-1306. (e) Snider, B. B.; Buckman, B. O. J. Org. Chem. 1992, 57, 322-326. (f) Alonso, R. A.; Burgey, C. S.; Rao, B. V.; Vite, G. D.; Vollerthun, R.; Zottola, M. A.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 6666-6672.
21. To our knowledge, a cyclization of a stabilized radical onto a nitrile function has not been reported previously. Nitriles as radical acceptors are sometimes problematic. For unsuccessful or low yield attempts of ε-cyano radical cyclizations, see: (a) Chenera, B.; Chuang, C.-P.; Hart, D. J.; Hsu, L.-Y. J. Org. Chem. 1985, 50, 5409-5410. (b) Yeung, B.-W. A.; Contelles, J. L. M.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1989, 1160-1162. Knapp, S. Gibson, F. S.; Choe, Y. H. Tetrahedron Lett. 1990, 31, 5397-5400. For successful examples, see: (d) Shono, T.; Kise, N. Tetrahedron Lett. 1990, 31, 1303-1306. (e) Snider, B. B.; Buckman, B. O. J. Org. Chem. 1992, 57, 322-326. (f) Alonso, R. A.; Burgey, C. S.; Rao, B. V.; Vite, G. D.; Vollerthun, R.; Zottola, M. A.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 6666-6672.
22. The peroxide was added in portions of 10 mol% each at 2 h intervals.