Irradiation of alpha,beta-unsaturated ketones (aliphatic, both open chain and cyclic as well as aryl substituted) in 1,3-dioxolane in the presence of a sensitizer (benzophenone or anthraquinone) led to 4-oxobutanal acetals in fair to excellent yield through a very simple procedure (workup in most cases by bulb-to-bulb distillation). The resulting acetals were irradiated to give 2-hydroxycyclobutanone ketals, again through a simple procedure that gave a good yield with open-chain aliphatic derivatives.
Photochemical synthesis of 4-oxobutanal acetals and of 2-hydroxycyclobutanone ketals
MELLA, MARIELLA;FRECCERO, MAURO;FAGNONI, MAURIZIO;ALBINI, ANGELO
1999-01-01
Abstract
Irradiation of alpha,beta-unsaturated ketones (aliphatic, both open chain and cyclic as well as aryl substituted) in 1,3-dioxolane in the presence of a sensitizer (benzophenone or anthraquinone) led to 4-oxobutanal acetals in fair to excellent yield through a very simple procedure (workup in most cases by bulb-to-bulb distillation). The resulting acetals were irradiated to give 2-hydroxycyclobutanone ketals, again through a simple procedure that gave a good yield with open-chain aliphatic derivatives.File in questo prodotto:
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