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

Masaichi Saito, Michio Nakamura, Tomoyuki Tajima, Michikazu Yoshioka

Research output: Contribution to journalArticle

59 Citations (Scopus)

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 - 2007
Externally publishedYes

Fingerprint

Acetylene
Alkynes
Lithium
Butadiene
1,4-dilithio-1,3-butadiene

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Reduction of phenyl silyl acetylenes with lithium : Unexpected formation of a dilithium dibenzopentalenide. / Saito, Masaichi; Nakamura, Michio; Tajima, Tomoyuki; Yoshioka, Michikazu.

In: Angewandte Chemie - International Edition, Vol. 46, No. 9, 2007, p. 1504-1507.

Research output: Contribution to journalArticle

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