Synthesis 2013; 45(3): 326-329
DOI: 10.1055/s-0032-1317861
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

A Revised Preparation of (4-Acetamido-2,2,6,6-tetramethylpiperidin-1-yl)oxyl and 4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium Tetrafluoroborate: Reagents for Stoichiometric Oxidations of Alcohols

Leon J. Tilley
a  Shields Science Center, Stonehill College, Easton, MA 02357, USA   Fax: +1(508)5651469   Email: [email protected]
,
James M. Bobbitt*
b  Department of Chemistry, University of Connecticut, Storrs CT 06269-3060, USA   Fax: +1(1860)4862981   Email: [email protected]
,
Stephanie A. Murray
a  Shields Science Center, Stonehill College, Easton, MA 02357, USA   Fax: +1(508)5651469   Email: [email protected]
,
Casey E. Camire
a  Shields Science Center, Stonehill College, Easton, MA 02357, USA   Fax: +1(508)5651469   Email: [email protected]
b  Department of Chemistry, University of Connecticut, Storrs CT 06269-3060, USA   Fax: +1(1860)4862981   Email: [email protected]
,
Nicholas A. Eddy
b  Department of Chemistry, University of Connecticut, Storrs CT 06269-3060, USA   Fax: +1(1860)4862981   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 01 August 2012

Accepted after revision: 20 November 2012

Publication Date:
21 December 2012 (online)


Abstract

Revised preparations of (4-acetamido-2,2,6,6-tetramethylpiperidin-1-yl)oxyl and the corresponding oxoammonium salt, 4-acetamido-2,2,6,6-tetramethyl-1-oxoammonium tetrafluoroborate are presented together with some of the important properties of these two oxidizing­ reagents.

 
  • References

  • 1 Bobbitt JM, Brückner C, Merbouh N. Org. React. (N. Y.) 2009; 74: 103
  • 2 Tebben L, Studer A. Angew. Chem. Int. Ed. 2011; 50: 5034
  • 3 Iwabuchi Y. J. Synth. Org. Chem., Jpn. 2008; 66: 1076
  • 4 Bobbitt JM. TCIMAIL 2011; (148) 2; Available online at http://www.tcichemicals.com/en/ap/support-download/tcimail/backnumber/article/146drE.pdf
  • 5 Bobbitt JM, Flores MC. L. Heterocycles 1988; 27: 509
  • 6 Bobbitt JM. J. Org. Chem. 1998; 63: 9367
  • 7 Bobbitt JM. Chem. Eng. News 1999; 77 (29): 6
  • 8 Breton T, Beshiardes G, Léger J.-M, Kokoh KB. Eur. J. Org. Chem. 2007; 1567
  • 9 Bartelson AL. Ph.D. Thesis. University of Connecticut; USA: 2011
  • 10 Merbouh N, Bobbitt JM, Brückner C. J. Org. Chem. 2004; 69: 5116
  • 11 Golubev VA, Zhdanov RI, Gida VM, Rozantsev EG. Russ. Chem. Bull. 1971; 768
  • 12 Ma Z, Bobbitt JM. J. Org. Chem. 1991; 56: 6110
  • 13 Mamros AN, Sharrow PR, Weller WE, Luderer MR, Fair JD, Pazehoski KO, Luderer MR. ARKIVOC 2011; (v): 23
  • 14 Qiu JC, Pradhan PP, Blanck NB, Bobbitt JM, Bailey WF. Org. Lett. 2012; 14: 350
  • 15 Hayashi M, Shibuya M, Iwabuchi Y. Org. Lett. 2012; 14: 154
  • 16 Eddy NA, Kelly CB, Mercadante MA, Leadbeater NE, Fenteany G. Org. Lett. 2012; 14: 498
  • 17 Pradhan PP, Bobbitt JM, Bailey WF. J. Org. Chem. 2009; 74: 9524
  • 18 Pradhan PP, Bobbitt JM, Bailey WF. Org. Lett. 2006; 8: 5485
  • 19 Richter H, García-Mancheño O. Eur. J. Org. Chem. 2010; 4460
  • 20 Richter H, García-Mancheño O. Org. Lett. 2011; 13: 6066
  • 21 Richter H, Rohlmann R, García-Mancheño O. Chem. Eur. J. 2011; 17: 11622
  • 22 Richter H, Fröhlich R, Daniliuc C.-G, García-Mancheño O. Angew. Chem. Int. Ed. 2012; 51
  • 23 The oxoammonium salt 6 is available from Tokyo Chemical Industry Co., Ltd. (TCI). Compounds 1 and 4 are industrial chemicals manufactured by TCI, BASF, and Evonik among others.
  • 24 Bragd PL, Besemer AC, van Bekkum H. Carbohydr. Polym. 2002; 49: 397
  • 25 Merbouh N, Bobbitt JM, Brückner C. J. Carbohydr. Chem. 2002; 21: 65
  • 26 Bobbitt JM, Guttermuth MC. F, Ma Z, Tang H. Heterocycles 1990; 30: 1131
  • 27 Merbouh N, Bobbitt JM, Brückner C. Org. Prep. Proced. Int. 2004; 36: 3
  • 28 Merbouh N. Synlett 2003; 1757
  • 29 Bobbitt JM, Merbouh N. Org. Synth. Coll. Vol. XI . John Wiley & Sons; London: 2009: 93
  • 30 Endo T, Miyazawa T, Shiihashi S, Okawara M. J. Am. Chem. Soc. 1984; 106: 3877