Direct Transformation of Primary Nitro Compounds into Nitriles with Sodium­ Dithionite

Baris Temelli; Canan Unaleroglu

doi:10.1055/s-0033-1370874

Synthesis, Table of Contents

Synthesis 2014; 46(10): 1407-1412
DOI: 10.1055/s-0033-1370874

paper

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

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Abstract

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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.

Key words

nitriles - sulfur - nitro compounds - synthetic methods - radicals

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References

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

2a Chiappe C, Pieraccini D, Saullo P. J. Org. Chem. 2003; 68: 6710
2b Mowry DT. Chem. Rev. 1948; 42: 189

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

Supplementary Material

Supporting Information

Direct Transformation of Primary Nitro Compounds into Nitriles with Sodium­ Dithionite

Direct Transformation of Primary Nitro Compounds into Nitriles with Sodium Dithionite