Reactions of alkenyl Fischer carbene complexes with ketene acetals: Formation of alkynes

Siu Ling B. Wang, Xuejun Liu, Miriam C. Ruiz, Vijay Gopalsamuthiram, William D. Wulff

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Alkenyl Fischer carbene complexes with an isopropoxy group on the carbene carbon will react with ketene acetals by 1,4-addition to give a zwitterionic intermediate, which undergoes subsequent internal isopropoxide transfer to generate a vinylidene complex. Either a hydrogen or phenyl group on the vinylidene carbon will undergo a formal 1,2-migration to give 4-pentynoate esters after hydrolysis of the intermediate orthoester.

Original languageEnglish (US)
Pages (from-to)5219-5224
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number23
DOIs
StatePublished - Nov 27 2006

Keywords

  • Fischer carbene complex
  • Ketene acetal
  • Michael addition
  • Rearrangement
  • Vinylidene complex

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