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Synlett 2005(13): 2115-2116
DOI: 10.1055/s-2005-872237
DOI: 10.1055/s-2005-872237
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York
Trichloroisocyanuric Acid (TCCA)
Further Information
Publication History
Publication Date:
20 July 2005 (online)
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Introduction
Trichloroisocyanuric acid (TCCA) is a stable and inexpensive industrial chemical usually used as bleaching agent and bactericide.
It has found applications in organic chemistry as a chlorinating agent or oxidant, [1] allowing thioacetalization of carbonyl compounds, conversion of alcohols to halides, carboxylic acids to acid chlorides, alkenes to chloroethers, N-nitrosation of N,N-dialkylamines, selective mononitration of phenols, oxidation of alcohols to carbonyl compounds, aldehydes to methyl esters, aldoximes to nitrile oxides, thiols to disulfides, selenols to diselenides, and sulfides to sulfoxides.
- 1 For a review, see:
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Yamaoka H.Moriya N.Ikunaka M. Org. Process Res. Dev. 2004, 8: 931 - 5
Zolfigol MA.Azarifar D.Maleki B. Tetrahedron Lett. 2004, 45: 2181 - 6
De Luca L.Giacomelli G.Nieddu G. Org. Lett. 2001, 3: 3041 - 7
De Luca L.Giacomelli G.Nieddu G. J. Org. Chem. 2003, 68: 4999 - 8
Zolfigol MA.Madrakian E.Ghaemi E. Synlett 2003, 2222 - 9
Wengert M.Sanseverino AM.Mattos MCS. J. Braz. Chem. Soc. 2002, 13: 700 - 10
Chen F.-E.Kuang Y.-Y.Daí H.-F.Lu L.Huo M. Synthesis 2003, 2629 - 11
Hiegel GA.Lewis JC.Bae JW. Synth. Commun. 2004, 34: 3449 - 12
Rodrigues RC.Aguiar AP. Synth. Commun. 2001, 31: 3075