627-20-3Relevant articles and documents
Poutsma,M.L.,Kartch,J.L.
, p. 6595 - 6604 (1967)
Preference for structural versus geometric isomerization in the BCl3-catalyzed thermal isomerizations of gaseous 1,2-dimethylcyclopropane
Kalra, Bansi L.,Clark, Kimber G.,Lewis, David K.
, p. 263 - 264 (1988)
The thermal isomerization reactions of gaseous cis- and trans-1,2-dimethylcyclopropane have been studied in the presence and absence of boron trichloride, in a static reactor at 574 3, but the normally slower structural rearrangements become the dominant reactions in the presence of catalyst. Mechanistic implications are discussed.
Horner et al.
, p. 4023 (1968)
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Brown,Zweifel
, p. 1512 (1959)
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Designing and synthesis of phosphine derivatives of Ru3(CO)12 – Studies on catalytic isomerization of 1-alkenes
Pandya, Chayan,Panicker, Rakesh R.,Senjaliya, Parth,Hareendran, M.K. Hima,Anju,Sarkar, Sibasis,Bhat, Haamid,Jha, Prakash C.,Rao, Koya Prabhakara,Smith, Gregory S.,Sivaramakrishna, Akella
, (2021/01/12)
A comparative investigation on the isomerization reactions of 1-alkenes to their corresponding 2-alkenes catalyzed Ru3(CO)12 (1), Ru3(CO)9(PEt3)3 (2) and Ru3(CO)10(dppe) (3), (where dppe = 1,2-bis(diphenylphosphino)ethane) is described. Both the complexes of types 2 and 3 were characterized by all analytical and spectroscopic data. The molecular structure of 2 was confirmed by single-crystal X-ray analysis. It is observed that the nature of phosphine ligands plays an important role in the isomerization of 1-alkenes. When the chelated diphosphine is used, the internal isomerization reaction by [Ru3(CO)10(dppe)] (3) is completed relatively in less time compared to other derivatives. As per the DFT calculations, the observed reaction rate for the alkene isomerization may be explained based on the relative stability of 1, 2, and 3. The CO abstraction step is highly feasible in 3, the least stable among the three, thus the reaction occurs at the highest rate. Due to the increased relative stability from 2 to 1, the reaction requires more time at elevated temperatures and the rate decreases as a consequence.
Carbonylative, Catalytic Deoxygenation of 2,3-Disubstituted Epoxides with Inversion of Stereochemistry: An Alternative Alkene Isomerization Method
Lamb, Jessica R.,Hubbell, Aran K.,MacMillan, Samantha N.,Coates, Geoffrey W.
supporting information, p. 8029 - 8035 (2020/05/01)
Reactions facilitating inversion of alkene stereochemistry are rare, sought-after transformations in the field of modern organic synthesis. Although a number of isomerization reactions exist, most methods require specific, highly activated substrates to achieve appreciable conversion without side product formation. Motivated by stereoinvertive epoxide carbonylation reactions, we developed a two-step epoxidation/deoxygenation process that results in overall inversion of alkene stereochemistry. Unlike most deoxygenation systems, carbon monoxide was used as the terminal reductant, preventing difficult postreaction separations, given the gaseous nature of the resulting carbon dioxide byproduct. Various alkyl-substituted cis- A nd trans-epoxides can be reduced to trans- A nd cis-alkenes, respectively, in >99:1 stereospecificity and up to 95% yield, providing an alternative to traditional, direct isomerization approaches.