Five-to-six membered ring-rearrangements in the reaction of 5-perfluoroalkyl-1,2,4-oxadiazoles with hydrazine and methylhydrazine

Journal of Organic Chemistry

Volumn 71, Issue 21, 2006, Pages 8106-8113

  Buscemi, Silvestre ^a   Pace, Andrea ^a   Piccionello, Antonio Palumbo ^a   Pibiri, Ivana ^a   Vivona, Nicolò ^a   Giorgi, Gianluca ^b   Mazzanti, Andrea ^c   Spinelli, Domenico ^c  

^a UNIVERSITY OF PALERMO   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRAZINOLYSIS; HYDRAZONES; METHYLHYDRAZINE; REGIOCHEMISTRY;

CHEMICAL BONDS; HYDRAZINE; REACTION KINETICS; SPECTROSCOPIC ANALYSIS; SUBSTITUTION REACTIONS;

ORGANIC COMPOUNDS;

ALKYL GROUP; AMIDE; BENZENE DERIVATIVE; CARBONYL DERIVATIVE; HYDRAZINE; HYDRAZONE DERIVATIVE; METHYLHYDRAZINE; OXADIAZOLE DERIVATIVE; PERFLUORO COMPOUND; REAGENT;

ARTICLE; BOULTON KATRITZKY REARRANGEMENT; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDRAZINOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS; RING OPENING; STEREOCHEMISTRY; STEREOSPECIFICITY; X RAY DIFFRACTION;

EID: 33750000563     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061251e     Document Type: Article

References (29)

1. See for example: (a) Boulton, A. J.; Katritzky, A. R.; Hamid, A. M. J. Chem. Soc. C 1967, 2005-2007.
2. (b) Afridi, A. S.; Katritzky, A. R.; Ramsden, C. A. J. Chem. Soc., Perkin Trans. 1 1976, 315-320.
3. (c) Ruccia, M.; Vivona, N.; Spinelli, D. Adv. Heterocycl. Chem. 1981, 29, 141-169.
4. (d) L'abbé, G. J. Heterocycl. Chem. 1984, 21, 627-638.
5. (e) Vivona, N.; Buscemi, S.; Frenna, V.; Cusmano, G. Adv. Heterocycl. Chem. 1993, 56, 49-154.
6. (f) Pace, A.; Pibiri, I.; Buscemi, S.; Vivona, N. Heterocycles 2004, 63, 2627-2648.
7. Van der Plas, H. C. Adv. Heterocycl. Chem. 1999, 74, 1-253.
8. (a) Hetzheim, A.; Möckel, K. Adv. Heterocycl. Chem. 1966, 7, 183-224.
9. (b) Reid, J. R.; Heindel, N. D. J. Heterocycl. Chem. 1976, 13, 925-926.
10. Sandström, J. Adv. Heterocycl. Chem. 1968, 9, 165-209.
11. Suwinski, J.; Pawlus, W.; Salwinska, E.; Swierczek, K. Heterocycles 1994, 37, 1511-1520.
12. Wermann, K.; Walther, M.; Günther, W.; Görls, H.; Anders, E. Tetrahedron 2005, 61, 673-685.
13. Buscemi, S.; Pace, A.; Pibiri, I.; Vivona, N.; Lanza, C. Z.; Spinelli, D. Eur. J. Org. Chem. 2004, 974-980.
14. (a) Bird, C. W. Tetrahedron 1985, 41, 1409-1414.
15. (b) Bird, C. W. Tetrahedron 1992, 48, 335-340.
16. For aromaticity criteria of five-membered heterocycles, see also: (a) Bean, G. P. J. Org. Chem. 1998, 63, 2497-2506.
17. (b) Katritzky, A. R.; Barczynski, P.; Musumarra, G.; Pisano, D.; Szafran, M. J. Am. Chem. Soc. 1989, 111, 7-15.
18. (c) Katritzky, A. R.; Jug, K.; Oniciu, D. C. Chem. Rev. 2001, 101, 1421-1449.
19. (d) Balaban, A. T.; Oniciu, D. C.; Katritzky, A. R. Chem. Rev. 2004, 104, 2777-2812.
20. Buscemi, S.; Pace, A.; Pibiri, I.; Vivona, N.; Spinelli, D. J. Org. Chem. 2003, 68, 605-608.
21. Buscemi, S.; Pace, A.; Palumbo Piccionello, A.; Macaluso, G.; Vivona, N.; Spinelli, D.; Giorgi, G. J. Org. Chem. 2005, 70, 3288-3291.
22. Pibiri, I.; Pace, A.; Buscemi, S.; Vivona, N.; Malpezzi, L. Heterocycles 2006, 68, 307-321.
23. 10 this product was reported as unidentified.
24. 10
25. 13N chemical shifts see: Martin, G. E.; Hadden, C. E. J. Nat. Prod. 2000, 63, 543-585
26. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
27. 15 chain.
28. Kolehmainen, E.; Gawinecki, R.; Oœmialowski, B. Trezbiatowska, K. Magn. Reson. Chem. 1997, 35, 778-784.
29. 6, this work).