Reactions of Ruthenium Carbenes of the Type (PPh3)2(X)2Ru=CH-CH=CPh2 (X = Cl and CF3COO) with Strained Acyclic Olefins and Functionalized Olefins

Zhe Wu, Sonbinh T. Nguyen, Robert H. Grubbs*, Joseph W. Ziller

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

232 Scopus citations

Abstract

Ruthenium carbene complexes of the type (PPh3)2(X)2Ru=CH—CH=CPh2 (1, X = Cl; 2, X = CF3COO) can react with strained acyclic olefins and functionalized olefins. Complex 1 reacts with methylenecyclopropane and methylenecyclobutane and their derivatives to generate new active ring-opening metathesis polymerization (ROMP) catalysts. The product from the reaction between 1 and ethyl vinyl ether decomposes through a bimolecular coupling pathway. Complex 2 reacts with functionalized terminal olefins, such as alkyl vinyl ether, enamine, and alkyl vinyl sulfide to give hetero-substituted carbene complexes. However, in the case of alkyl vinyl ether, the resulting alkoxymethylenecarbene complex decomposes to ruthenium carbonyl species at room temperature. Complex 2 can also isomerize allylic vinyl ether or alcohol. Aromatic amines can react with 2 by first coordinating trans to the carbene ligand; a fact which indicates that the potential coordination site for olefin metathesis may be trans to the carbene moiety. The reactivity pattern of 2 with ftmctionalized vinyl olefins suggests that this reaction is best understood under the context of a Lewis acid/Lewis base interaction.

Original languageEnglish (US)
Pages (from-to)5503-5511
Number of pages9
JournalJournal of the American Chemical Society
Volume117
Issue number20
DOIs
StatePublished - Jan 1 1995

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Reactions of Ruthenium Carbenes of the Type (PPh<sub>3</sub>)2(X)<sub>2</sub>Ru=CH-CH=CPh<sub>2</sub> (X = Cl and CF<sub>3</sub>COO) with Strained Acyclic Olefins and Functionalized Olefins'. Together they form a unique fingerprint.

Cite this