Journal
TETRAHEDRON LETTERS
Volume 49, Issue 19, Pages 3063-3066Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.03.058
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The reaction of benzenediazonium carboxylate with chloroform in refluxing tetrahydrofuran afforded 5,5,5-trichloropentyl phenyl ether in 61% yield along with benzoic acid (7%). When dichloroacetonitrile was used as a reactant, 5,5-dichloro-5-cyanopentyl phenyl ether was obtained in 65% yield. Reactive benzyne derived from diazonium carboxylate initially reacted with THF to give a dipole intermediate, which further reacted with chloroform or dichloroacetonitrile to give ring opened products. (C) 2008 Elsevier Ltd. All rights reserved.
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