Brønsted acid TfOH-mediated reactions of methylenecyclopropanes with nitriles

Synlett

Volumn , Issue 13, 2004, Pages 2343-2346

  Huang, Jin Wen ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

3+2 cycloaddition; Acetonitrile; Benzonitrile; Br nsted acid; Methylenecyclopropanes; Ritter reaction

Indexed keywords

ACID; BRONSTED ACID; CYCLOPROPANE DERIVATIVE; METHYLENECYCLOPROPANE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; QUANTUM YIELD; REACTION ANALYSIS; RING OPENING; RITTER REACTION;

EID: 8644226896     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-832838     Document Type: Article

References (30)

1. For synthesis of MCPs: (a) Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 598.
2. (b) Carbocyclic Three-Membered Ring Compounds, InHouben-Weyl, Vol. E17; deMeijere, A., Ed.; Thieme: Stuttgart, 1996.
3. (c) For reviews on the reaction of MCPs, please see: Nakamura, I.; Yamamoto, Y. Adv. Synth. Catal. 2002, 344, 111.
4. (d) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213.
5. (a) Shi, M.; Xu, B. Org. Lett. 2002, 4, 2145.
6. (b) Shi, M.; Chen, Y.; Xu, B.; Tang, J. Tetrahedron Lett. 2002, 43, 8019.
7. (c) Xu, B.; Shi, M. Org. Lett. 2003, 5, 1415.
8. (d) Chen, Y.; Shi, M. J. Org. Chem. 2004, 69, 426.
9. (e) Huang, J.-W.; Shi, M. Tetrahedron Lett. 2003, 44, 9343.
10. (f) On the other hand, Kilburn reported Lewis acid mediated cascade reactions of silyl-substituted methylenecyclopropane with ketones and aldehydes: Peron, G. L. N.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2000, 41, 1615.
11. (g) Peron, G. L. N.; Norton, D.; Kitteringham, J.; Kilburn, J. D. Tetrahedron Lett. 2001, 42, 347.
12. (h) Patient, L.; Berry, M. B.; Kilburn, J. D. Tetrahedron Lett. 2003, 44, 1015.
13. (i) Nuske, H.; Erase, S.; Kozhushkov, S. I.; Noltemeyer, M.; Es-Sayed, M.; de Meijere, A. Chem.-Eur. J. 2002, 8, 2350.
14. (j) Mizuno, K.; Nire, K.; Sugita, H.; Otsuji, Y. Tetrahedron Lett. 1993, 34, 6563.
15. For a review of homoallylic rearrangement, please see: (a) Sarel, S.; Yovell, J.; Sarel-Imber, M. Angew. Chem. 1968, 80, 592.
16. (b) For Brønsted acid-catalyzed reactions of MCPs 1 see: Dunkelblum, E. Isr. J. Chem. 1973, 11, 557.
17. (c) Chiusoli, G. P.; Costa, M.; Melli, L. J. Organomet. Chem. 1988, 358, 495.
18. (d) Danskaya, N. A.; Kozhushkov, S. I.; Kuznetsova, T. S.; Lukin, K. A.; Kazimirchik, I. V. J. Org. Chem. (USSR) (Engl. Transl.) 1981, 17, 1874.
19. (e) Siriwardana, A. I.; Nakamura, I.; Yamamoto, Y. Tetrahedron Lett. 2003, 44, 985.
20. (f) Dehmlow, E. V. Z. Naturforsch., B: Chem. Sci. 1988, 358, 495.
21. (a) Ritter, J. J. J. Am. Chem. Soc. 1952, 74, 763.
22. (b) Krimel, L. I. Org. React. 1969, 17, 215.
23. (c) Ichikawa, Y. Yuki Gosei Kagaku Kyokaishi 1997, 55, 281.
24. 2 is therefore required.
25. 000 = 1056; diffractometer: Rigaku AFC7R; residuals: R, Rw: 0.0432, 0.0784.
26. Benzonitrile is used as the reactant and the solvent because many MCPs 1 are dissolved very well in benzonitrile.
27. (a) Olah, G. A.; von Schleyer, P. R. Carbonium Ions, Vol. 1; Wiley: New York, 1968, 45-47.
28. (b) Olah, G. A.; SuryaPrakash, G. K.; Sommer, J. Super Acids; Wiley: New York, 1985, 85.
29. (c) Danishefsky, S. Acc. Chem. Res. 1979, 66, 12.
30. Utimoto, K.; Tamura, M.; Sisido, K. Tetrahedron 1973, 29, 1169.