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
1993
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
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