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Paper | Special issue | Vol 82, No. 2, 2010, pp.1195-1202
Published online, 7th September, 2010
DOI: 10.3987/COM-10-S(E)30
Nucleophilic Reactions of 9-Isopropyl-2,4-dimethoxy-7,12-dimethyl-3-(phenylsulfonyl)benzo[a]heptalene with Lithium Dialkylamides

Samir El Rayes, Anthony Linden, Khaled Abou-Hadeed, and Hans-Jürgen Hansen*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Abstract

Treatment of the title compounds with lithium piperidinide in THF at –5 °C leads to an exchange of the two methoxy groups by piperidino substituents (Scheme 2). On the other hand, lithium diisopropylamide (LDA) in THF at –5 °C induces the formation heptaleno-annulated dibenzothiophenes.