Chlorination of aromatic systems with trichloroisocyanuric acid under polar and free-radical conditions

Juenge, Eric C.; Beal, David A.; Duncan, W. P.

doi:10.1021/jo00828a039

Cited by 56 publications

(27 citation statements)

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“…The potential of trichloro-s-triazinetrione as a substitute for chlorine in the halogenation of aromatic systems was noted some time ago [13] but did not elicit much interest. [14] The few synthetic reports demonstrated the high chlorination potency that led to multiple chlorination products.…”

Section: Resultsmentioning

confidence: 99%

Room‐Temperature Electrophilic 5‐endo‐dig Chlorocyclization of Alk‐3‐yn‐1‐ones with the Use of Pool Sanitizer: Synthesis of 3‐Chlorofurans and 5‐Chlorofuropyrimidine Nucleosides

et al. 2008

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The 5-endo-dig chlorocyclization of 1,4-disubstituted alk-3-yn-1-ones (propargylic ketones) with the use of trichloro-striazinetrione (trichloroisocyanuric acid, TCCA; 0.4 equiv.) in toluene, at room temperature, in the absence of base, provides 2,5-disubstituted 3-chlorofurans in high yields (79-96 %). The reaction can be accomplished by using commercially available swimming pool sanitizer. Selected 3-chlo-

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Section: Resultsmentioning

confidence: 99%

Room‐Temperature Electrophilic 5‐endo‐dig Chlorocyclization of Alk‐3‐yn‐1‐ones with the Use of Pool Sanitizer: Synthesis of 3‐Chlorofurans and 5‐Chlorofuropyrimidine Nucleosides

et al. 2008

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“…It was said that trichloroisocyanuric acid can act not only as an oxidant but a chlorinating reagent [35]. Juenge et al [36] have observed that the chlorination of aromatic systems using trichloroisocyanuric acid, with electron-rich groups, occurred easily; with electron-withdrawing groups, did not occur. The chlorinated compounds were either ortho-isomers or para-isomers.…”

Section: Resultsmentioning

confidence: 99%

Selective oxidation and chlorination of trifluoromethylsulfide using trichloroisocyanuric acid in ionic liquid

Tang

Zhong

Lin

2007

Journal of Fluorine Chemistry

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“…O uso do ácido tricloroisocianúrico (1) em reações de substituição eletrofílica aromática (SEAr) pode ser feito em soluções polares, na presença de um agente iniciador de radicais livres 13 (Esquema 4). Elas podem ser realizadas em solução aquosa de áci-do sulfúrico 50% (v/v) ou na presença de um ácido de Lewis, como cloreto férrico.…”

Section: Cloração Via Searunclassified

Cloreto isocianúrico e cloreto cianúrico: aspectos gerais e aplicações em síntese orgânica

Cunha¹,

Paixão²,

Souza³

et al. 2006

Quím. Nova

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Recebido em 10/2/05; aceito em 13/7/05; publicado na web em 8/2/06 ISOCYANURIC CHLORIDE ACID AND CYANURIC CHLORIDE: GENERAL ASPECTS AND APPLICATIONS IN ORGANIC SYNTHESIS. The aromatic six-membered heterocycles having three nitrogen atoms are denominated triazines. Among these heterocycles, isocyanuric chloride and cyanuric chloride are inexpensive and readily available 1,3,5-triazine derivatives, which have been attracting significant attention of organic chemists due to their different kinds of applications, which vary from pharmaceuticals to explosives. This short overview explores their uses in synthetic methods, as chlorinating and oxidating agents and some procedures for their preparation.

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Chlorination of aromatic systems with trichloroisocyanuric acid under polar and free-radical conditions

Cited by 56 publications

References 1 publication

Room‐Temperature Electrophilic 5‐endo‐dig Chlorocyclization of Alk‐3‐yn‐1‐ones with the Use of Pool Sanitizer: Synthesis of 3‐Chlorofurans and 5‐Chlorofuropyrimidine Nucleosides

Room‐Temperature Electrophilic 5‐endo‐dig Chlorocyclization of Alk‐3‐yn‐1‐ones with the Use of Pool Sanitizer: Synthesis of 3‐Chlorofurans and 5‐Chlorofuropyrimidine Nucleosides

Selective oxidation and chlorination of trifluoromethylsulfide using trichloroisocyanuric acid in ionic liquid

Cloreto isocianúrico e cloreto cianúrico: aspectos gerais e aplicações em síntese orgânica

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