Carbolithiation of aromatic rings: cyclohexadienes from N-aroyl-2,2,6,6-tetramethylpiperidines

Benzamides whose nitrogen atom is part of a 2,2,6,6-tetramethylpiperidine ring are dearomatised by alkyllithiums, which attack them regioselectively to yield, after electrophilic quench, substituted cyclohexadienes.

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Bibliographic Details
Published inChemical communications (Cambridge, England) no. 18; pp. 2138 - 2139
Main Authors Clayden, J, Foricher, YJY, Lam, HK
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.09.2002
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
NATURAL-PRODUCTS
ORGANOLITHIUMS
STRATEGIES
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Summary:Benzamides whose nitrogen atom is part of a 2,2,6,6-tetramethylpiperidine ring are dearomatised by alkyllithiums, which attack them regioselectively to yield, after electrophilic quench, substituted cyclohexadienes.
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ISSN:1359-7345
1364-548X
DOI:10.1039/b206479k