Iron(III) Chloride as Mild and Efficient Reagent for the α-Thiocyanation of Ketones: An Expedient Synthesis of α-Oxo Thiocyanates

Jhillu S. Yadav; Basi V. Subba Reddy; Ummareddy V. Subba Reddy; Darshanoju N. Chary

doi:10.1055/s-2008-1072517

PAPER

Iron(III) Chloride as Mild and Efficient Reagent for the α-Thiocyanation of Ketones: An Expedient Synthesis of α-Oxo Thiocyanates

Jhillu S. Yadav*, Basi V. Subba Reddy, Ummareddy V. Subba Reddy, Darshanoju N. Chary
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512.; e-Mail: yadav@iict.res.in;

Abstract

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Abstract

A simple and efficient method for the α-thiocyanation of ketones has been developed; anhydrous iron(III) chloride is used under mild conditions to produce α-oxo thiocyanates in good to high yields and with high selectivity. The use of inexpensive and readily available iron(III) chloride makes this procedure simple, convenient, and practical.

Key words

thiocyanation - ketones - iron(III) chloride - catalysis - α-oxo thiocyanates

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References

1 Wood JL. Organic Reactions Vol. 3: Adams R. John Wiley & Sons; New York: 1946. Chap. 6.

2a Metzer JB. Comprehensive Heterocyclic Chemistry Vol. 6: Katritzky A. Pergamon; Oxford: 1984. p.235

2b Yadav LDS. Patel R. Rai VK. Srivastava VP. Tetrahedron Lett. 2007, 48: 7793

3 Kawamura S, Izumi K, Satoh J, Sanemitsu Y, Hamada T, Shibata H, and Satoh R. inventors; Pat. Appl. EP 446802. ; Chem. Abstr. 1992, 116, 59360j

4a Shahidi F. Sulphur Compounds in Foods Mussinan CJ. Keelan ME. American Chemical Society; Washington DC: 1984. Chap. 9. p.1067-1286

4b Mehta RG. Liu J. Constantinou A. Thomas CF. Hawthorne M. You M. Gerhaeuser C. Pezzuto JM. Moon RC. Moriarty RM. Carcinogenesis 1995, 16: 399

5 Guy RG. In The Chemistry of Cyanates and Their Thio Derivatives Part 2: Patai S. John Wiley & Sons; New York: 1977. Chap. 18. p.819

6 Bacon RGR. Guy RG. J. Chem. Soc. 1961, 2428

7 Dittmer DC. Comprehensive Heterocyclic Chemistry Vol. 7: Katritzky A. Pergamon; Oxford: 1984. p.178

8 Prakash O. Saini N. Synth. Commun. 1993, 23: 1455

9a Prakash O. Kaur H. Batra H. Rani N. Singh SP. Moriarty RM. J. Org. Chem. 2001, 66: 2019

9b Prakash O. Rani N. Sharma V. Moriarty RM. Synlett 1997, 1255

10 Atkins EF. Dabbs S. Guy RG. Mahomed AA. Mountford P. Tetrahedron 1994, 50: 7253

11a Bolm C. Legros J. Paiti JL. Zani L. Chem. Rev. 2004, 104: 6217

11b Ruping M. Nactshim BJ. Scheidt T. Org. Lett. 2006, 8: 3717

11c Komeyma K. Morimoto T. Takaki K. Angew. Chem. Int. Ed. 2006, 45: 2938

11d Kischel J. Jovel I. Mertins K. Zapf A. Beller M. Org. Lett. 2006, 8: 19

11e Diaz DD. Miranda PO. Padron JI. Martin VS. Curr. Org. Chem. 2006, 10: 457

11f Iovel I. Kristin M. Kischel J. Zapf A. Mathias B. Angew. Chem. Int. Ed. 2005, 44: 3913

12 Kumar A. Ahamd P. Maurya RA. Tetrahedron Lett. 2007, 48: 1399