Collect. Czech. Chem. Commun.
1987, 52, 2926-2935
https://doi.org/10.1135/cccc19872926
Arbuzov rearrangement in the reaction of arylmethylenemalonaldehydes with trimethyl phosphite: Formation of 2-(α-dimethoxyphosphonylbenzyl)-3-methoxyacroleins
Dalimil Dvořák, David Šaman, Miloš Buděšínský and Zdeněk Arnold
Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
Abstract
Reaction of arylmethylenemalonaldehydes I with trimethyl phosphite affords substituted methoxyacroleins V. The reaction proceeds via intermediates VII which, according to spectral data, can be described as interconverting dipolar and cyclic structures VIIA and VIIB, respectively. The intermediates VII are easily hydrolyzed to give the substituted malonaldehydes VI. Compounds VI were also obtained by acid-catalyzed hydrolysis of methoxyacroleins V.
