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Synlett 2011(14): 2069-2071  
DOI: 10.1055/s-0030-1261178
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Hypochlorite-Induced Ipso-Substitution Reactions of Aromatic Alcohols and Related Compounds

Hector V. Carrilloa, Angelica Y. Rodrigueza, Robert G. Landolt*a, William H. Hendricksonb
a Department of Chemistry, Texas Wesleyan University, Fort Worth, TX 76105, USA
Fax: +1(871)5314275; e-Mail: rlandolt@txwes.edu;
b Department of Chemistry, University of Dallas, Irving, TX 75062, USA
Further Information

Publication History

Received 13 May 2011
Publication Date:
10 August 2011 (online)

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Abstract

Organic solvent extracts derived from aqueous hypochlorite/phase-transfer catalyst solutions induce rapid and efficient ipso substitution of aromatic carbinols and related substrates. The key parameter impacting rates and yields is pH of the original hypochlorite/phase-transfer catalyst component.

Key words

alcohols - electrophilic aromatic substitution - halogenation - phase-transfer catalysis - solvent effects

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13

Carrillo, H.; Rodriguez, A.; Melendez, J.; Oropeza, M.; Ngo, M.; Woods, G.; Landolt, R. G. Hypochlorite-Induced IPSO Reactions of an Aromatic Alcohol; Poster 215, 64th Southwest Regional ACS Meeting, Little Rock, AR. 2008 (accessed August 2010), http://acs.confex.com/acs/swrm08/techprogram/P60964.HTM, accessed December, 2010.