80137-82-2Relevant academic research and scientific papers
Methylenecyclopropanes IX. - Methylenecyclopentanes by Metal-Catalyzed Cycloaddition of 1-Methylene-2-(trimethylsilyl)cyclopropane with Electron-Deficient Olefins
Binger, Paul,Sternberg, Ethan,Wittig, Ute
, p. 1933 - 1938 (2007/10/02)
Monocyclic cyclopentanes such as 2a-c as well as certain bicyclic derivatives are prepared in high yields by cycloadditions of 1-methylene-2-(trimethylsilyl)cyclopropane (1) with electron-deficient olefins catalyzed by triisopropylphosphane containing palladium(0) compounds.The trimethylsilyl group can be easily displaced by protolysis with trifluoroacetic acid yielding the methylenecyclopentanes 6a-c or 9a and 10a.Therefore, 1 can be regarded as a synthetic equivalent of methylenecyclopropane.
Reactions of Methylenecyclopropanes, V. Palladium(0)-catalyzed Codimerisation of Methylenecylopropane with Methyl Acrylates and 1,2-Ethylenedicarbonic Esters
Binger, Paul,Schuchardt, Ulf
, p. 3313 - 3324 (2007/10/02)
Triorganylphosphane-modified palladium(0) compounds catalyze the codimerisation of methylenecyclopropane (1) with methyl acrylate, methyl trans-crotonate or trans-cinnamate to give the methylenecyclopentanecarboxylic esters 3, 4, 5; diethyl fumarate or dimethyl maleate and 1 lead to the methylenecyclopentanedicarbonic esters 12.With diethyl maleate besides cis/trans-12b also oligomers containing two mols of 1 and one (cis/trans-14) or two mols of the diester (cis/trans-15) are formed.
