105-38-4Relevant articles and documents
A novel synthesis of vinyl esters from vinylversatate-10
Mondal,Van Der Meer,German,Heikens
, p. 4205 - 4207 (1974)
Vinylversatate-10 (VV10)1 1 VV 10 Vinyl Monomer, Development Product, Shell Chemical Company has successfully been used to synthesise a large number of lower vinyl esters by transvinylation in presence of mercuric acetate and sulfuric acid. The synthesis of vinylhalo esters proceeds with more difficulty. It has been observed that neither Hg(OAc)2 nor H2SO4 alone is capable of initiating the transvinylation. Furthermore, it has been found that a molar ratio 2:1 of VV10 to carboxylic acid is sufficient to drive the reaction to the right by continuous distillation of the vinyl ester formed, and as a result a high yield of vinyl ester is obtained. A mechanism for this reaction and for the formation of side products has been proposed.
Ruthenium-catalyzed transvinylation - New insights
Ziriakus, Jennifer,Zimmermann, Teresa K.,P?thig, Alexander,Drees, Markus,Haslinger, Stefan,Jantke, Dominik,Kühn, Fritz E.
, p. 2845 - 2859 (2014/03/21)
The use of ruthenium complexes in transvinylation catalysis has been well established since the 1980s. However, the reaction mechanism and the active catalyst species, which is presumed to contain ruthenium carbonyl carboxylate entities, have so far remained elusive. In this work the synthesis and characterization of three novel ruthenium complexes comprising ruthenium carbonyl carboxylate structural motifs including two single crystal structures as well as the crystal structures of two known ruthenium complexes are reported. These new complexes and four known ruthenium complexes with appropriate structural motifs were applied in transvinylation catalysis. Mechanistic studies including identification and characterization of the active species, isotope labeling experiments and examination of the regioand stereoselectivity of the transvinylation reaction are presented, resulting in the proposal of a probable reaction mechanism, which is supported by DFT calculations on the B3LYP/6-31G* level of theory.
Competitive reactivity as a probe for reaction coordinates in gas-phase ion-molecule chemistry
Holman, Robert W.,Sumpter, Terry L.,Farrar, John,Weigel, Kurt,Bartmess, John E.
, p. 585 - 589 (2007/10/03)
Using the method of competitive reactivity of two functional groups in the same molecule, anionic elimination reactions show considerable kinetic selectivity for small differences in leaving group thermochemistry, in structures of the general type YCH2CH2CH2Z, where Y and Z are good anionic leaving groups.
