112439-12-0Relevant academic research and scientific papers
Copper-catalyzed coupling of 1,1-dibromo-1-alkenes with phenols: A general, modular, and efficient synthesis of ynol ethers, bromo enol ethers, and ketene acetals
Jouvin, Kevin,Bayle, Alexandre,Legrand, Frederic,Evano, Gwilherm
supporting information; experimental part, p. 1652 - 1655 (2012/06/05)
An efficient and general copper-catalyzed method is reported for the synthesis of phenol-derived 1-bromoenol ethers, ynol ethers, and ketene acetals by chemodivergent copper-catalyzed cross-coupling between readily available 1,1-dibromo-1-alkenes and phen
Copper-mediated selective cross-coupling of 1,1-dibromo-1-alkenes and heteronucleophiles: Development of general routes to heterosubstituted alkynes and alkenes
Jouvin, Kevin,Coste, Alexis,Bayle, Alexandre,Legrand, Frederic,Karthikeyan, Ganesan,Tadiparthi, Krishnaji,Evano, Gwilherm
, p. 7933 - 7947 (2013/01/16)
Efficient and general procedures for the cross-coupling of 1,1-dibromoalkenes and N-, O-, and P-nucleophiles are reported. Fine-tuning of the reaction conditions allows for either site-selective, double, or alkynylative cross-coupling, therefore providing
A Facile Synthesis of Ketene O,N-Acetals and Ketene O,O-Acetals by Tosylate Elimination
Reuther, Wolfgang,Ruland, Alfred,Baus, Ulf
, p. 235 - 240 (2007/10/02)
Reaction of the alcohols 4 and 5 with p-toluensulfonyl chloride leads to the sulfonic esters 6 and 7, respectively, which on treatment with potassium tert-butylate easily react to give the ketene O,N-acetals 8 and O,O-acetals 9, respectively.The (E/Z) isomers 8 arising from the elimination reaction of 7 were identified by their 1H-NMR data after X-ray analysis of one of the isomers of 8e.On one example it is shown that the elimination reaction proceeds stereoselectively "anti".
