Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 20
260
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

Superoxide‐Mediated Regioselective Deblocking of the Tosyl Group from N‐Tosylcarboxamides

&
Pages 3075-3078 | Received 08 Feb 2006, Published online: 16 Feb 2007

References

  • Greene , T. W. and Wuts , P. G. M. 1991 . Protective Groups in Organic Synthesis , 2nd ed. New York : Wiley .
  • Kocienski , P. 1994 . Protecting Groups Stuttgart : Thieme Verlag .
  • Entwistle , I. D. and Wood , W. W. 1991 . Comprehensive Organic Synthesis Edited by: Trost , B. M. and Fleming , I. Vol. 8 , Oxford : Pergamon Press .
  • Sabitha , G. , Reddy , B. V. S. , Abraham , S. and Yadav , J. S. 1999 . Deprotection of sulfonamide using iodotrimethylsilane . Tetrahedron Lett. , 40 ( 8 ) : 1569 – 1570 . and references cited therein
  • Alonso , E. , Ramon , D. J. and Yus , M. 1997 . Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene‐catalysed lithiation . Tetrahedron , 53 ( 42 ) : 14355 – 14368 .
  • Haskins , C. M. and Knight , D. W. 2004 . Efficient indole N‐tosylation using thioglycolate . Tetrahedron Lett. , 45 ( 3 ) : 599 – 601 . and references cited therein
  • Casadei , M. A. , Gessner , A. , Inesi , A. , Jugelt , W. and Moracci , F. M. 1992 . Electrodic cleavage of the N‐S bond in N‐tosylcarboxamides: A new entry to N‐unsubstituted lactams . J. Chem. Soc., Perkin Trans. 1 , : 2001 – 2004 .
  • Knowles , H. , Parsons , A. F. and Pettifer , R. M. 1997 . Desulfonylation of amides using samarium iodide . Synlett , : 271 – 272 .
  • Parsons , A. F. and Pettifer , R. M. 1996 . A radical approach to N‐desulfonylation . Tetrahedron Lett. , 37 ( 10 ) : 1667 – 1670 .
  • Singh , S. , Verma , M. and Singh , K. N. 2004 . Superoxide induced oxidation of γ‐lactones to γ‐ketocarboxylic acids in aprotic medium . Synth. Commun. , 34 ( 24 ) : 4471 – 4475 .
  • Singh , S. and Singh , K. N. 2005 . Superoxide‐mediated synthesis of N‐aminoaziridines from N‐aminoheterocycles and olefins . Synth. Commun. , 35 ( 19 ) : 2597 – 2602 .
  • Singh , K. N. and Kumar , R. 2005 . Some studies on the reaction of in‐situ generated tetraethylammonium superoxide with 2‐oxazolin‐5‐ones . Indian J. Chem. , 44B : 381 – 386 .
  • Shukla , A. K. , Verma , M. and Singh , K. N. 2004 . Superoxide induced deprotection of 1,3‐dithiolanes: A convenient method of dedithioacetalization . Indian J. Chem. , 43B : 1748 – 1752 .
  • Kemp , A. D. and Stephen , H. 1948 . The preparation of some N‐substituted derivatives of p‐toluenesulphonamide . J. Chem. Soc. , : 110 – 112 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.