Synthesis 2014; 46(10): 1407-1412
DOI: 10.1055/s-0033-1370874
paper
© Georg Thieme Verlag Stuttgart · New York

Direct Transformation of Primary Nitro Compounds into Nitriles with Sodium­ Dithionite

Baris Temelli*
Hacettepe University, Department of Chemistry, 06800 Ankara, Turkey   Fax: +90(312)2992163   eMail: temelli@hacettepe.edu.tr
,
Canan Unaleroglu
Hacettepe University, Department of Chemistry, 06800 Ankara, Turkey   Fax: +90(312)2992163   eMail: temelli@hacettepe.edu.tr
› Institutsangaben
Weitere Informationen

Publikationsverlauf

Received: 06. Januar 2014

Accepted after revision: 06. Februar 2014

Publikationsdatum:
11. März 2014 (online)


Abstract

A new and practical direct transformation of primary nitro compounds into nitriles with sodium dithionite is described. The reaction is simple, convenient and eliminates the use of expensive and moisture-sensitive reagents.

Supporting Information

 
  • References

    • 1a Fatiadi AJ In Preparation and Synthetic Applications of Cyano Compounds. Patai S, Rappaport Z. Wiley; New York: 1983
    • 1b Smith MB, March J In March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 6th ed. Wiley; New Jersey: 2007
    • 3a Alterman M, Hallberg A. J. Org. Chem. 2000; 65: 7984
    • 3b Schareina T, Zapf A, Beller M. Chem. Commun. 2004; 1388
    • 3c Yang C, Williams JM. Org. Lett. 2004; 6: 2837
    • 3d Sundermeier M, Zapf A, Beller M. Angew. Chem. Int. Ed. 2003; 42: 1661
    • 4a Arote ND, Bhalerao DS, Akamanchi KG. Tetrahedron Lett. 2007; 48: 3651
    • 4b Sharghi H, Sarvari MH. Tetrahedron 2002; 58: 10323
    • 5a Oishi T, Yamaguchi K, Mizuno N. Angew. Chem. Int. Ed. 2009; 48: 6286
    • 5b Iida S, Togo H. Tetrahedron 2007; 63: 8274
    • 5c Reddy KR, Maheswari CU, Venkateshwar M, Prashanthi S, Kantam ML. Tetrahedron Lett. 2009; 50: 2050
    • 6a Yang SH, Chang S. Org. Lett. 2001; 3: 4209
    • 6b Zhou S, Addis D, Das S, Junge K, Beller M. Chem. Commun. 2009; 4883
    • 6c Yamaguchi K, Fujiwara H, Ogasawara Y, Kotani M, Mizuno N. Angew. Chem. Int. Ed. 2007; 46: 3922
    • 6d Ishihara K, Furuya Y, Yamamoto H. Angew. Chem. Int. Ed. 2002; 41: 2983
    • 6e Kuo C.-W, Zhu J.-L, Wu J.-D, Chu C.-M, Yao C.-F, Shia K.-S. Chem. Commun. 2007; 301
    • 6f Choi E, Lee C, Na Y, Chang S. Org. Lett. 2002; 4: 2369
    • 6g Singh MK, Lakshman MK. J. Org. Chem. 2009; 74: 3079
    • 6h Zhou S, Junge K, Addis D, Das S, Beller M. Org. Lett. 2009; 11: 2461
    • 7a Do H.-Q, Daugulis O. Org. Lett. 2010; 12: 2517
    • 7b Yan G, Kuang C, Zhang Y, Wang J. Org. Lett. 2010; 12: 1052
    • 7c Jia X, Yang D, Wang W, Luo F, Cheng J. J. Org. Chem. 2009; 74: 9470
    • 7d Chen X, Hao X.-S, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 6790
    • 7e Mariampillai B, Alliot J, Li M, Lautens M. J. Am. Chem. Soc. 2007; 129: 15372
    • 8a Denis JN, Krief A. Tetrahedron Lett. 1979; 41: 3995
    • 8b Mukaiyama T, Nambu H. J. Org. Chem. 1962; 27: 2201
    • 8c Wehrli PA, Schaer B. J. Org. Chem. 1977; 42: 3956
    • 8d Tu Z, Jang Y, Lin C, Liu J.-T, Hsu J, Sastry MN. V, Yao C.-F. Tetrahedron 2005; 61: 10541
    • 9a Olah GA, Vankar YD, Gupta BG. B. Synthesis 1979; 36
    • 9b Tsay S.-C, Gani P, Hwu JR. J. Chem. Soc., Perkin Trans. 1 1991; 1493
  • 10 Olah GA, Narang SC, Field LD, Fung AP. J. Org. Chem. 1983; 48: 2766
  • 11 Chang RK, Kim K. Tetrahedron Lett. 1996; 37: 7791
  • 12 Czekelius C, Carreira EM. Angew. Chem. Int. Ed. 2005; 44: 612
    • 13a Fieser LF, Fieser M In Reagents for Organic Synthesis. Vol. 1. Wiley; New York: 1980: 1081
    • 13b Fieser LF, Fieser M In Reagents for Organic Synthesis. Vol. 8. Wiley; New York: 1980: 456
    • 13c Fieser LF, Fieser M In Reagents for Organic Synthesis. Vol. 9. Wiley; New York: 1980: 426
    • 14a Redemann CT, Redemann CE. Org. Synth., Coll. Vol. 1955; 3: 69
    • 14b Park KK, Oh CH, Sim W.-J. J. Org. Chem. 1995; 60: 6202
    • 14c Yang D, Fokas D, Li J, Yu L, Baldino CM. Synthesis 2005; 47
    • 15a de Vries JG, Kellogg RM. J. Org. Chem. 1980; 45: 4126
    • 15b Chung S.-K. J. Org. Chem. 1981; 46: 5457
  • 16 Pojer PM. Aust. J. Chem. 1979; 32: 201
  • 17 Janzen EG. J. Phys. Chem. 1972; 76: 157
  • 18 Zollinger H In Color Chemistry: Syntheses, Properties, and Applications of Organic Dyes and Pigments. Wallmann PM. Wiley-VCH; Weinheim: 2003: 306-310
  • 19 Long JA, Harris NJ, Lammertsma K. J. Org. Chem. 2001; 66: 6762
  • 20 Mowry DT. Chem. Rev. 1948; 42: 189
    • 21a Lin C, Hsu J, Sastry MN. V, Fang H, Tu Z, Liu J-T, Ching-Fa Y. Tetrahedron 2005; 61: 11751
    • 21b Lu X, Lin S. J. Org. Chem. 2005; 70: 9651
  • 22 Wang J, Masui Y, Onaka M. ACS Catal. 2011; 1: 446
  • 23 Bhalerao DS, Mahajan US, Chaudhari KH, Akamanchi KG. J. Org. Chem. 2007; 72: 662