Ortho-selective nucleophilic aromatic substitution reactions of polyhaloanilines with potassium/sodium O-ethyl xanthate: A convenient access to halogenated 2(3H)-benzothiazolethiones

Journal of Organic Chemistry

Volumn 69, Issue 21, 2004, Pages 7371-7374

  Zhu, Lei ^a   Zhang, Mingbao ^a  

^a BAYER CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HALOGEN COMPOUNDS; NEGATIVE IONS; POTASSIUM; SUBSTITUTION REACTIONS; SULFUR;

CYCLIZATION; NUCLEOPHILES; ORTHO-SELECTIVE;

AROMATIC COMPOUNDS;

2 MERCAPTOBENZOTHIAZOLE; 2(3H) BENZOTHIAZOLETHIONE; ANILINE DERIVATIVE; AROMATIC COMPOUND; HALOGEN; POLYHALOANILINE; POTASSIUM; SODIUM O ETHYL XANTHATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HALOGENATION; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 5444239745     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049056s     Document Type: Article

References (16)

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10. - is more exposed for nucleophilic attack, similar to the crown ether effect.
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12. 1H NMR).
13. Precoordination of reactants via noncovalent forces can have dramatic effects on reactivity by bringing the reactive sites in close proximity. For a recent example, see: Gatti, F. G.; Leigh, D. A.; Nepogodiev, S. A.; Slawin, A. M. Z.; Teat, S. J.; Wong, J. K. J. Am. Chem. Soc. 2001, 123, 5983-5989.
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16. 1H NMR. No reaction between the aniline and the xanthate was observed after 6 h (in the absence of a reaction with aniline, sodium O-ethyl xanthate undergoes slow decomposition under these conditions). This observation is consistent with the fact that aniline substrates lacking an ortho halogen were recovered under the reaction conditions (entries 1-3, Table 3).