53282-12-5Relevant articles and documents
A two-step ball milling method synthesizes and purifies α,β-unsaturated esters
Shearouse, William C.,Korte, Chelsea M.,Mack, James
experimental part, p. 598 - 601 (2011/05/08)
Over the last decade, solvent-free methods have been gaining interest as replacements for traditional organic chemistry techniques. While solvent-free methods are well known for many processes, a simple, solvent-free purification procedure that supplements them does not exist. We report the solvent-free synthesis of α,β-unsaturated esters using a solvent-free Horner-Wadsworth-Emmons (HWE) reaction using high-speed ball milling (HSBM). We were able to perform the HWE reaction on a variety of aldehydes, and isolate their respective a,b-unsaturated esters in high yields, purities, and diastereoselectivities. The Royal Society of Chemistry.
REACTIONS DE WITTIG-HORNER ET DE TRANSESTERIFICATION EN UNE OPERATION PAR ACTIVATION ANIONIQUE DE LIAISONS C-H ET O-H EN MILIEU HETEROGENE CARBONATE DE POTASSIUM/ALCOOL
Mouloungui, Z.,Elmestour, R.,Delmas, M.,Gaset, A.
, p. 1219 - 1232 (2007/10/02)
The Wittig-Horner reaction carried out in various alcohols is accompanied by transesterification of the alkyl radical of the α,β-ethylenic ester formed.The occurrence of these two reactions in the same reaction medium is affected by the behavior of: i) the alcohol (solvent and reagent), ii) potassium carbonate (reagent and catalyst).The propensity for the two reactions to occur was found to depend on the polarity of the alcohol.Protic alcohols speeded both the Wittig-Horner and the subsequent transesterification reaction.Both reactions were quantitative despite the use of non-stoichiometric amounts of potassium carbonate.Regeneration in situ of the solid base observed in aprotic medium was markedly enhanced under these reaction conditions.The mechanism proposed for these two reactions incorporates this regeneration process.
BASE AND ACID DECOMPOSITION OF UNSATURATED 1-ACYL-2-TOSYLHYDRAZINES
Bellesia, Franco,Grandi, Romano,Pagnoni, Ugo M.,Trave, Roberto
, p. 511 - 514 (2007/10/02)
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