Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 6
636
Views
31
CrossRef citations to date
0
Altmetric
Original Articles

A Green Preparation of N-Chloro- and N-Bromosaccharin

, &
Pages 935-939 | Received 03 Apr 2002, Published online: 17 Aug 2006

References

  • Dolenc , D. 2000 . N-Iodosaccharin—A new reagent for iodination of alkenes and activated aromatics . Synlett , 4 : 544 – 546 .
  • Fairbanks , A.J. and Aloui , M. 2001 . N-Iodosaccharin: A potent new activator of thiophenylglycosides . Synlett , 6 : 797 – 799 .
  • Gakh , A.A. , Romaniko , S.V. , Ugrak , B.I. and Fainzilberg , A.A. 1991 . N-Fluorination with cesium fluoroxysulfate . Tetrahedron , 47 ( 35 ) : 7447 – 7458 .
  • Chauhan , R.P.S. , Ahmed , I. and Kumar , A. 1995 . Determination of milligram amounts of thiourea, allylthiourea and phenylthiourea using N-chlorosaccharin in acetic-acid media . Asian J. Chem. , 7 ( 3 ) : 667 – 668 . (Chem. Abstr. 1995, 123, 245771p)
  • Das , C.M. 1991 . Determination of some sulfur-compounds with N-bromoimides . Talanta , 38 ( 3 ) : 347 – 350 . (Chem. Abstr. 1991, 114, 258834a)
  • Khan , M.U. , Verma , J.K. , Nigam , S.K. , Parihar , S.S. and Dwiverdi , H.P. 1998 . Kinetics and mechanistic approach on N-chlorosaccharin oxidation of some aliphatic aldehydes . Oxid. Commun. , 21 ( 3 ) : 362 – 368 .
  • Sharma , V.K. , Sharma , K. , Gupta , H.D. and Gupta , P.P. 1995 . Kinetics of oxidation of benzaldehyde and substituted benzaldehydes by N-bromosaccharin in aqueous acetic acid-perchloric acid medium . Oxid. Commun. , 18 ( 4 ) : 395 – 406 .
  • Manoharan , V. and Venkatasubramanian , N. 1986 . Kinetics of oxidation of aliphatic secondary alcohols by N-bromosaccharin . J. Indian Chem. Soc. , 63 ( 6 ) : 613 – 615 .
  • Bachhawat , J.M. and Mathur , N.K. 1971 . Oxidation of secondary alcohols, glycols, α-hydroxy acids, amino acids and hydrocarbons by N-bromosaccharin . Indian J. Chem. , 9 ( 12 ) : 1335 – 1336 .
  • Manikyamba , P. and Sundaram , E.V. 1980 . Kinetics of oxidation of amino-acids by N-bromosaccharin . Indian J. Chem. , 19A ( 11 ) : 1122 – 1124 .
  • Zajc , B. 1999 . Synthesis of (+/−)-trans-7,8-Dihydrodiol of 6-fluoro-benzo[a] pyrene via hydroxyl-directed regioselective functionalization of Substituted Pyrene . J. Org. Chem. , 64 ( 6 ) : 1902 – 1907 .
  • Mozek , I. and Sket , B. 1992 . Chlorination and bromination of molecules by an N-halosaccharin/pyridinium poly(hydrogen fluoride) system . Synth. Commun. , 22 ( 17 ) : 2513 – 2520 .
  • Bachhawat , J.M. , Koul , A.K. , Prashad , B. , Ramegowd , N.S. , Narang , C.K. and Mathur , N.K. 1973 . Allylic and Benzylic chlorination and oxidation of organic substrate using N-chlorosaccharin . Indian J. Chem. , 11 ( 6 ) : 609 – 610 .
  • Sanchez , E.I. and Fumarola , M.J. 1982 . N-Bromosaccharin: Benzylic and α-carbonylic bromination . J. Org. Chem. , 47 ( 8 ) : 1588 – 1590 .
  • Panchatsharam , V.S. , Sundaram , S. and Venkatasubramanian , N. 1981 . Chlorination of ketones with N-chlorosaccharin . Indian J. Chem. , 20A ( 5 ) : 469 – 472 .
  • Zajc , B. 1999 . A convenient preparation of N-bromosaccharin, source of electrophilic bromine . Synth. Commun. , 29 ( 10 ) : 1779 – 1784 .
  • Sanchez , E.I. and Fumarola , M.J. 1976 . A new synthesis of N-bromosaccharin using bromine chloride . Synthesis , 11 : 736 – 737 .
  • Chattaway , F.D. 1905 . A contribution to the chemistry of o-Benzoic Sulphinida . J. Chem. Soc. , 87 ( 2 ) : 1882 – 1887 .
  • Curini , M. , Epifani , F. , Marcotullio , M.C. , Rosati , O. and Tsadjout , A. 2000 . N-chlorination of amides and carbamates by oxone® and sodium chloride . Synlett , 6 : 813 – 814 .
  • Dieter , R.K. , Nice , L.E. and Velu , S.E. 1996 . Oxidation of α,β-enones and alkenes with oxone and sodium halides: A convenient laboratory preparation of chlorine and bromine . Tetrahedron Lett. , 37 ( 14 ) : 2377 – 2380 .
  • Clark , J.H. 1999 . Green chemistry: Challenges and opportunities . Green Chem. , 1 ( 1 ) : 1 – 8 .
  • Anastas , P.T. and Warner , J.C. 2000 . Green Chemistry: Theory and Practice Oxford : Oxford University Press .

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.