95599-91-0Relevant academic research and scientific papers
Ozonolysis of β-(Alkoxycarbonyl)- and β-Acyl-Substituted Vinyl Ethers. Cycloaddition Chemistry of the Derived α-Keto Ester O-Oxides and α-Diketone O-Oxides
Sugiyama, Tomohito,Yamakoshi, Hideyuki,Nojima, Masatomo
, p. 4211 - 4218 (2007/10/02)
Ozonolyses of a series of vinyl ethers 1a-h having electron-withdrawing substituent(s) at the β-position were carried out in methanol and also in aprotic solvents in the presence of 1,3-dipolarophiles.Methanol-trapping experiments revealed that the cleavage of the primary ozonides from vinyl ethers 1a,b,d-f is regioselective, providing in each case the corresponding α-keto ester O-oxides 3a,b and α-diketone O-oxides 3d-f.These electron-deficient carbonyl oxides 3a,b,d-f could undergo cycloadditions with a variety of 1,3-dipolarophiles, particularly nitrones, and give in each case the corresponding cycloadducts.
