Nucleophilic substitution accompanying carbon-carbon bond cleavage assisted by a nitro group

Bulletin of the Chemical Society of Japan

Volumn 80, Issue 12, 2007, Pages 2413-2417

  Nakaike, Yumi ^a   Taba, Noriko ^b   Itoh, Shinobu ^c   Tobe, Yoshito ^a   Nishiwaki, Nagatoshi ^b   Ariga, Masahiro ^b  

^a OSAKA UNIVERSITY   (Japan)

^b OSAKA KYOIKU UNIVERSITY   (Japan)

^c Osaka Prefecture University

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM SALTS; BOND CLEAVAGES; CARBON BOND CLEAVAGES; INTRAMOLECULAR REACTIONS; KETO ESTERS; MALONIC ACIDS; MILD CONDITIONS; NITRO GROUPS; NUCLEOPHILIC SUBSTITUTIONS; UNSYMMETRICAL;

AMINATION; AMINES; AMMONIUM COMPOUNDS; CARBOXYLIC ACIDS; ESTERS; NITRATION; SALTS;

ORGANIC COMPOUNDS;

EID: 43849096211     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.80.2413     Document Type: Article

References (28)

1. a) O. V. Larionov, S. I. Kozhushkov, A. de Meijere, Synthesis 2005, 158.
2. b) S. Olivella, A. Solé, Ó. Jiménez, M. P. Bosch, A. Guerrero, J. Am. Chem. Soc. 2005, 127, 2620.
3. c) O. Jiménez, M. P. Bosch, A. Guerrero, J. Org. Chem. 2005, 70, 10883.
4. d) G. Papeo, H. Posteri, D. Borghi, M. Varasi, Org. Lett. 2005, 7, 5641.
5. Y. Nakaike, Y. Kamijo, S. Mori, M. Tamura, N. Nishiwaki, M. Ariga, J. Org. Chem. 2005, 70, 10169.
6. a) T. Suzuki, C. Okada, K. Arai, A. Awaji, T. Shimizu, K. Tanemura, T. Horaguchi, J. Heterocycl. Chem. 2001, 38, 1409.
7. b) T. L. Gilchrist, A. Rahman, J. Chem. Soc., Perkin Trans. 1 1998, 1203.
8. c) A. Ahibo-Coffy, J.-C. Promé, Tetrahedron Lett. 1976, 17, 1503.
9. The acetyl group was activated by an adjacent acyl group, which in turn served as a leaving group: a) A. R. Katritzky, Z. Wang, M. Wang, C. R. Wilkerson, C. D. Hall, N. G. Akhmedov, J. Org. Chem. 2004, 69, 6617.
10. b) S. Nakatsu, A. T. Gubaidullin, V. A. Mamedov, S. Tsuboi, Tetrahedron 2004, 60, 2337.
11. Deacylation was reported in which acyl group was activated by electron-withdrawing effect of a bromo group and a steric effect of bulky group: Y. Hu, D. Bai, Tetrahedron Lett. 1998, 39, 2375.
12. The acyl group of 3-oxoesters is activated by bulky aryl group. N. Nishiwaki, D. Nishida, T. Ohnishi, F. Hidaka, S. Shimizu, M. Tamura, K. Hori, Y. Tohda, M. Ariga, J. Org. Chem. 2003, 68, 8650.
13. R. Ballini, G. Bosica, D. Fiorini, Tetrahedron 2003, 59, 1143.
14. T. Simmons, K. L. Kreus, J. Org. Chem. 1968, 33, 836.
15. A. L. Laikhter, V. P. Kislyi, V. V. Semenov, Mendeleev Commun. 1993, 20.
16. When 3-nitro-2,4-pentanedione was left in the air at room temperature for about a day, acetic acid and unidentified products were obtained. This result indicates that the diketone reacts with ambient moisture. Hence, a less reactive 2-nitro-3-oxoester was employed, because of its relative stability in the air.
17. a) A. J. Clark, C. P. Dell, J. M. McDonagh, J. Geden, P. Mawdsley, Org. Lett. 2003, 5, 2063.
18. b) R. V. Hoffman, S. Madan, J. Org. Chem. 2003, 68, 4876.
19. c) A. Luna, I. Alfonso, V. Gotor, Org. Lett. 2002, 4, 3627.
20. d) G. W. Spears, K. Tsuji, T. Tojo, H. Nishimura, T. Ogino, J. Heterocycl. Chem. 2002, 39, 799.
21. V. F. Kucherov, L. A. Yanovskaya, in The Chemistry of Functional Group, ed. by S. Patai, Interscience-Publishers, London, 1969, pp. 175-209.
22. A. Goeta, M. M. Salter, H. Shah, Tetrahedron 2006, 62, 3582.
23. N. Shindo, K. Tamura, Meiji Daigaku Nogakubu Kenkyu Hokoku 1988, 80, 29;
24. Chem. Ahstr. 1989, 110, 19783p.
25. Ethyl choloroformylacetate has also been prepared from symmetrical diethyl malonate by selective chemical conversion, a) M. Fonvielle, H. Therisod, M. Hemery, M. Therisod, Bioorg. Med. Chem. Lett. 2007, 17, 410.
26. b) V. G. S. Box, N. Marinovic, G. P. Yiannikouros, Heterocycles 1991, 32, 245.
27. c) T. Kametani, T. Katoh, M. Tsubuki, T. Honda, Chem. Pharm. Bull. 1985, 33, 61.
28. R. Shelkov, M. Nahmany, A. Melman, J. Org. Chem. 2002, 67, 8975.