135513-95-0Relevant articles and documents
Preparation and Selected Reactions of t-Butyl 2-Methylene-3-oxoalkanoates
Hoffmann, H. Martin R.,Gassner, Andreas,Eggert, Ulrike
, p. 2475 - 2480 (2007/10/02)
The title class of 1,1-diactivated ethylenes has been prepared in two steps from aldehydes and t-butyl acrylate by (i) DABCO-catalyzed coupling to give t-butyl 2-(hydroxyalkyl)-2-propenoates 11 and (ii) low-temperature Jones oxidation, followed by swift work up at low temperature.The resulting butyl 2-methylene-3-oxoalkanoates 12 are stabilized by sterically demanding and also by aromatic groups R.For primary unhindered alkyl groups, stability is low.The compounds enter into Michael reactions, hetero Diels-Alder additions with enol ethers, and self-dimerization.Key Words: Ethylenes, 2,2-diactivated/ Michael acceptors/ 1-Oxa-1,3-butadienes/Hetero Diels-Alder reaction