Synthesis and reactivity of achiral and of a novel planar chiral thioferrocenoylsilanes

Bianca F. Bonini, Mauro Comes-Franchini, Mariafrancesca Fochi, Germana Mazzanti, Alfredo Ricci, Massimiliano Tomasulo, Greta Varchi

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

The reactions of thioferrocenoylsilanes with organolithium reagents, dienes and reducing agents which afford α-silyl sulphides, dihydrothiopyranes and α-silyl ferrocenyl thiols, respectively, have been investigated. α-Silyl sulphides were further functionalised through carbodesilylation with aldehydes. We also report the synthesis of a new planar chiral thioferrocenoylsilane that gave good diastereomeric excess in the reaction with t-butyllithium, lithium lutidine and 2,3-dimethylbuta-1,3-diene. The 1,1′-bis-thioferrocenoylsilane, too unstable to be isolated, was trapped in situ with dienes.

Original languageEnglish (US)
Pages (from-to)407-417
Number of pages11
JournalJournal of Organometallic Chemistry
Volume637-639
DOIs
StatePublished - Dec 3 2001

Keywords

  • Diels-Alder reaction
  • Ferrocene
  • Planar chirality
  • Thioacylsilanes
  • Thiophilic addition
  • β-Amino sulphides
  • β-Hydroxy sulphides

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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