Rapid Markovnikov Addition of HCl to a Pendant Alkyne: Evidence for a Quinoidal Cumulene

Samantha Eaves, S.J. Hart, A.C. Whitwood, D.S. Yufit, Paul Low, J.M. Lynam

Research output: Contribution to journalArticle

6 Citations (Scopus)
205 Downloads (Pure)

Abstract

Reaction of cis-[RuCl2(dppm)2]BF4 with TlBF4 and 1,4-diethynyl-benzenes results in the formation of the vinylidene cations trans-[Ru([double bond, length as m-dash]C[double bond, length as m-dash]CH–C6H2-2,5-R2-4-C[triple bond, length as m-dash]CH)Cl(dppm)2]+ (R = H, Me). Subsequent reaction with [NnBu4]Cl results in nucleophilic attack at the coordinated organic ligand, but not at the expected metal-bound carbon atom. Instead, trans-[Ru(C[triple bond, length as m-dash]C–C6H2-2,5-R2-4-CCl[double bond, length as m-dash]CH2)Cl(dppm)2] was generated which, when coupled with DFT calculations, provides evidence for an intermediate quinoidal cumulene complex.
Original languageEnglish
Pages (from-to)9362-9365
JournalChemical Communications
Volume51
Issue number45
DOIs
Publication statusPublished - 7 Jun 2015

Fingerprint Dive into the research topics of 'Rapid Markovnikov Addition of HCl to a Pendant Alkyne: Evidence for a Quinoidal Cumulene'. Together they form a unique fingerprint.

Cite this