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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 3
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Original Articles

Unexpected C-C bond cleavage of α-nitroketone in the presence of TsNBr2: A new pathway for C-N bond formation

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Pages 257-262 | Received 26 Oct 2015, Published online: 06 Feb 2016

References

  • (a) Bode, J. W. Top. Organomet. Chem. 2013, 44, 13; (b) Pattabiraman, V. R.; Bode, J. W. Nature 2011, 480, 471; (c) Collet, F.; Lescot, C.; Dauban, P. Chem. Soc. Rev. 2011, 40, 1926; (d) Chang, J. W. W.; Ton, T. M.U.; Chan, P. W. H.; Chem. Record 2011, 11, 331; (e) Joullié, M. M.; Lassen, K. M. Arkivoc 2010, 8, 189; (f) Valeur, E.; Bradley, M. hem. Soc. Rev., 2009, 38, 606; (g) Montalbetti, C. A. G. N.; Falque, V. M. in Wiley Encyclopedia of Chemical Biology; Wiley, New York, 2008; p. 1; (h) Moody, C. J. Comprehensive Organic Synthesis; B. M. Trost and I. Fleming, Eds.; Pergamon: Oxford, UK, 1991; vol. 7, p. 21; (i) Muller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905; (j) Dıaz-Requejo, M. M.; Perez, P. J. Chem. Rev. 2008, 108, 3379; (k) Collet, F.; Dodd, R. H.; Dauban, P. Chem. Commun. 2009, 5061.
  • (a) Fructos, M. R.; Trofimenko, S.; Diaz-Requejo, M. M.; Perez, P. J. J. Am. Chem. Soc. 2006, 128, 11784; (b) Albone, D. P.; Challenger, S.; Derrick, A. M.; Fillery, S. M.; Irwin, J. L.; Parson, C. M.; Takada, H.; Taylor, P. C.; Wilson, D. J. Org. Biomol. Chem. 2005, 3, 107; (c) Bhuyan, R.; Nicholas, K. M. Org. Lett. 2007, 9, 3957; (d) Phukan, P. Sudalai, A. Tetrahedron: Asymmetry 1998, 9, 1001.
  • (a) Chanda, B. M., Vyas, R., Bedekar, A. V. J. Org. Chem. 2001, 66, 30; (b) Harden, J. D.; Ruppel, J. V.; Gao, G.-Y.; Zang, X. P. Chem. Commun. 2007, 4644; (d) Sharma, C. M.; Kashyap, B.; Phukan, P. Indian J. Chem. 2014, 53B, 750; (g) Borah, A. J.; Phukan, P. Tetrahedron Lett. 2014 55, 713.
  • (a) Lebel, H.; Huard, K. Org. Lett. 2007, 9, 639; (b) Huard, K.; Lebel, H. Chem. Eur. J. 2008, 14, 6222.
  • (a) Omura, K.; Murakami, M.; Uchida, T.; Irie, R.; Katsuki, T. Chem. Lett. 2003, 354; (b) Liu, Y.; Che, C.-M. Chem. Eur. J. 2010, 16, 10494.
  • (a) Shen, R.; Huang, X. J. Org. Chem. 2007, 72, 3961; (b) Shen, R.; Huang, X.; Org. Lett. 2009, 11, 5698; (c) Zhi, S.; An, G.; Sun, H.; Han, J.; Li, G.; Pan, Y. Tetrahedron Lett. 2010, 51, 2745; (d) Saikia, I.; Kashyap, B.; Phukan, P. Chem. Commun. 2011, 47, 2967; (e) Borah, A. J.; Phukan, P. Chem. Commun. 2012, 48, 5491.
  • (a) Phukan, P.; Chakraborty, P.; Kataki, D. J. Org. Chem. 2006, 71, 7533; (b) Saikia, I.; Phukan, P. Tetrahedron Lett. 2009, 50, 5083; (c) Saikia, I.; Kashyap, B.; Phukan, P. Synth. Commun. 2010, 40, 2647; (d) Saikia, I.; Rajbongshi, K. K.; Phukan, P. Tetrahedron Lett. 2012, 53, 758; (e) Borah, A. J.; Phukan, P. Tetrahedron Lett. 2012, 53, 3035; (f) Rajbongshi, K. K.; Phukan, P. Tetrahedron Lett. 2014, 55, 1877; (g) Rajbongshi, K. K.; Sarma, M. J.; Phukan, P. Tetrahedron Lett. 2014, 55, 5358; (h) Rajbongshi, K. K.; Hazarika, D.; Phukan, P. Tetrahedron Lett. 2015, 56, 356; (i) Saikia, I.; Chakraborty, P.; Sarma, M. J.; Goswami, M.; Phukan, P. Synth. Commun. 2015, 45, 211.
  • (a) Ballini, R.; Bosica, G.; Fiorini, D.; Palmieri, A. Tetrahedron 2005, 61, 8971; (b) Lu, R.-J.; Yan, Y.-Y.; Wang, J.-J.; Du, Q.-S.; Nie, S.-Z.; Yan, M. J. Org. Chem. 2011, 76, 6230; (c) Songhui, C.; Donghu, B.; Feng, S.; Jian, L.; Chunju, L.; Xueshun, J. Chin. J. Chem. 2012, 30, 1464; (d) Tan, X.; Liu, B.; Li, X.; Li, B.; Xu, S.; Song, H.; Wang, B. J. Am. Chem. Soc. 2012, 134, 16163; (e) Yang, Y.; Gao, M.; Deng, C.; Zhang, D.-X.; Wu, L.-M.; Shu, W.-M.; Wu, A.-X. Tetrahedron 2012, 68, 6257; (f) Giorgi, G.; López-Alvarvdo, P.; Miranda, S.; Rodriguuez, J.; Menéndez, J. C. Eur. J. Org. Chem. 2013, 2013, 1327; (g) Nguyen, H. H.; Kurth, M. J. Org. Lett. 2013, 15, 362; (h) Zhou, Y.-Q.; Wang, N.-X.; Xing, Y.; Wang, Y.-J.; Hong, X.-W.; Zhang, J.-X.; Chen, D.-D.; Geng, J.-B.; Dang, Y.; Wang, Z.-X. Sci. Reports 2013, 3, 1058; (i) Lain, Z.; Friis, S. D.; Skrydstrup, T. Chem. Commun. 2015, 51, 3600.
  • Young, A. J.; White, M. C.; Angew. Chem. Int. Ed. 2011, 50, 6824.
  • (a) Bernasconi, C. F.; Montañez, R. L. J. Org. Chem. 1997, 62, 8162; (b) Lee, J. J.; Kim, J.; Jun, Y. M.; Lee, B. M.; Kim, B. H. Tetrahedron 2009, 65, 8821.
  • Lodh, R.; Sarma, M. J.; Borah, A. J.; Phukan, P. Monatsh. Chem. 2015, 146, 969.
  • Nair, C. G. R.; Indrasen, P. Talanta 1976, 23, 239.

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