Reduction of phenyl silyl acetylenes with lithium: Unexpected formation of a dilithium dibenzopentalenide

Masaichi Saito, Michio Nakamura, Tomoyuki Tajima, Michikazu Yoshioka

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Abstract

(Chemical Equation Presented) The degree of bulkiness of the silyl substituent strongly affects the reduction mode of phenyl silyl acetylenes. For example, the treatment of phenyl(triisopropylsilyl)acetylene with lithium led to the unprecedented formation of a dilithium dibenzopentalenide together with the expected 1,4-dilithio-1,3-butadiene (see scheme), whereas the reduction of phenyl(tert-butyldimethylsilyl)acetylene gave only the corresponding 1,4-dilithio-1,3-butadiene.

Original languageEnglish
Pages (from-to)1504-1507
Number of pages4
JournalAngewandte Chemie - International Edition
Volume46
Issue number9
DOIs
Publication statusPublished - Jun 27 2007

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Keywords

  • Alkynes
  • Aromatic systems
  • Intermolecular cyclization
  • Metalation
  • Reduction

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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