Preparation and trapping of 3-lithium-O-lithiophenoxide

3-Bromophenol and 3-Bromothiophenol are converted into the title compounds by proton abstraction followed by halogen-metal exchange with tert-butyllithium. The resulting dianions are then trapped on carbon with various electrophiles. 3-Bromophenol and 3-Bromothiophenol are converted into the title c...

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Bibliographic Details
Published inTetrahedron letters Vol. 34; no. 13; pp. 2043 - 2046
Main Authors Selnick, Harold G., Bourgeois, Michelle L., Butcher, John W., Radzilowski, Ellen M.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 26.03.1993
Elsevier
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
DIRECTED ORTHO-LITHIATION
Lithiation
Carbohydroxamic acid
Halophenols
Benzenic compound
Organic dianion
Carbanion
Electrophilic reaction
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Summary:3-Bromophenol and 3-Bromothiophenol are converted into the title compounds by proton abstraction followed by halogen-metal exchange with tert-butyllithium. The resulting dianions are then trapped on carbon with various electrophiles. 3-Bromophenol and 3-Bromothiophenol are converted into the title compounds treatment with tert-butyllithium. The resulting dianions are then trapped on carbon with various electrophiles.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)60341-6