RuO4-Mediated oxidation of secondary amines 2. Imines as main reaction intermediates

Main Article Content

Cristina Antoneta Florea
Anca Hîrtopeanu
Cristina Stavarache
Horia Petride

Abstract

Oxidation by RuO4 (generated in situ from RuO2 and NaIO4) of secondary amines like Bn-NH-CH2R (1; R=H, Me) gave complex reaction mixtures, but mainly amides. In the presence of cyanide, the leading products were α-aminonitriles. Comparison of the oxidation products of 1 with those from the corresponding imines PhCH=N-CH2R and Bn-N=CH-R showed that formation of the indicated imines is the first main step in the oxidation of 1. A detailed mechanism is proposed.

Downloads

Metrics

PDF views
850
Aug 01 '17Aug 04 '17Aug 07 '17Aug 10 '17Aug 13 '17Aug 16 '17Aug 19 '17Aug 22 '17Aug 25 '17Aug 28 '175.0
| |

Article Details

How to Cite
[1]
C. A. Florea, A. Hîrtopeanu, C. Stavarache, and H. Petride, “RuO4-Mediated oxidation of secondary amines 2. Imines as main reaction intermediates”, J. Serb. Chem. Soc., vol. 82, no. 6, pp. 627–640, Aug. 2017.
Section
Organic Chemistry

References

D. Chatterjee, A. Mitra, B. C. Roy, J. Mol. Catal., A: Chem. 161 (2000) 17

C.-M. Che, J.-L. Zhang, R. Zhang, J.-S. Huang, T.-S. Lai, W.-M. Tsui, X.-G. Zhou, Z.-Y. Zhou, N. Zhu, C. K. Chang, Chem.-Eur. J. 11 (2005) 7040

K. Yamaguchi, N. Mizuno, Chem.-Eur. J. 9 (2003) 4353

K. Yamaguchi, N. Mizuno, J. Jpn. Pet. Inst. 57 (2014) 251

K. Yamaguchi, N. Mizuno, Angew. Chem. Int. Ed. 42 (2003) 1480

S.-I. Murahashi, T. Naota, K. Yonemura, J. Am. Chem. Soc. 110 (1988) 8256

J. M. Bakke, A. E. Frøhaug, J. Phys. Org. Chem. 9 (1996) 310

M. Drees, T. Strassner, J. Org. Chem. 71 (2006) 1755

B. Plietker, M. Niggeman, Org. Lett. (2003) 3353

J. K. Beattie, Pure Appl. Chem. 62 (1990) 1145

S.-I. Murahashi, T. Nakae, H. Terai, N. Komiya, J. Am. Chem. Soc. 130 (2008) 11005

S.-I. Murahashi, N. Komiya, H. Terai, T. Nakae, J. Am. Chem. Soc. 125 (2003) 15312

H. Petride, C. Drăghici, C. Florea, A. Petride, Cent. Eur. J. Chem. 2 (2004) 302

H. Petride, C. Drăghici, C. Florea. A. Petride, Cent. Eur. J. Chem. 4 (2006) 674

H. Petride, O. Costan, C. Drăghici, C. Florea, A. Petride, ARKIVOC (Gainesville, FL, U.S.) X (2005) 18

B. Plietker, Synthesis (2005) 2453

S.-I. Murahashi, T. Naota, H. Taki, J. Chem. Soc., Chem. Commun. (1985) 613

K.-N. T. Tsenq, N. K. Szymczek, Synlett 25 (2014) 2385

S.-I. Murahashi, Y. Okano, H. Sato, T. Nakae, N. Komiya, Synlett 11 (2007) 1675

A. J. Bailey, B. R. James, Chem. Commun. (1996) 2343

A. Goti, M. Romani, Tetrahedron Lett. 35 (1994) 6567

S.-I. Murahashi, in Transition Metals for Organic Synthesis, M. Beller, C. Bolm, Eds., Wiley–VCH, Weinheim, 2004, pp. 497–523

W. P. Griffith, in Catalysis by Metal Complexes, C. Bianchini, D. J. Cole-Hamilton, P. W. N. M. van Leeuwen, Eds., Springer, Dordrecht, 2011, pp. 1–134 and 227–234

D. Balan, H. Adolfson, J. Org. Chem. 66 (2001) 6498

K. Hattori, Y. Yamamoto, J. Org. Chem. 57 (1992) 3264

A. Córdova, Acc. Chem. Res. 37 (2004) 102

Part 1: C. A. Florea, H. Petride, J. Serb. Chem. Soc. 81 (2016) 475

F. Texier-Boullet, Synthesis (1985) 679

A. F. Bella, L. V. Jackson, J. C. Walton, Org. Biomol. Chem. 2 (2004) 421

A. Makhloufi, W. Frank, C. Ganter, Organometallics 31 (2012) 2001

R. T. Lewis, W. B. Motherwell, Tetrahedron 48 (1992) 1465

H. Moehrle, U. Scharf, E. Ruehmann, Arch. Pharm. (Weinheim) 316 (1983) 251

A. R. Katritzky, B. Pilarski, L. Urogdi, J. Chem. Soc., Perkin Trans. 1 (1990) 541

N. Sakai, N. Takahashi, D. Inoda, R. Ikeda, T. Konahara, Molecules 18 (2013) 12488

C. Florea, C. Stavarache, H. Petride, Rev. Roum. Chim. 61 (2016) 321

R. V. Jagadeesh, H. Junge and M. Beller, ChemSusChem 8 (2015) 92

L. Cristian, S. Nica, O. D. Pavel, C. Mihailciuc, V. Almăşan, S. M. Coman, C. Hardacre, V. I. Pârvulescu, Catal. Sci. Technol. 3 (2013) 2646

S. Aiki, A. Taketoshi, J. Kuwabara, T. Koizumi, T. Kanbara, J. Organomet. Chem. 696 (2011) 1301

Y. Zhang, K. Xu, X. Chen, T. Hu, Y. Yu, J. Zhang, J. Huang, Catal. Commun. 11 (2010) 951

I. W. C. E. Arends, T. Kodama, R. A. Sheldon, Top. Organomet. Chem. 11 (2004) 277

T. Naota, H. Takaya, S.-I. Murahashi, Chem. Rev. 98 (1998) 2599

S. Torii, T. Inokuchi, K. Kondo, J. Org. Chem. 50 (1985) 4980

D. Yang, C. Zhuang, J. Org. Chem. 66 (2001) 4814.