Photochemical synthesis of 4-oxobutanal acetals and of 2-hydroxycyclobutanone ketals

Citation
C. Manfrotto et al., Photochemical synthesis of 4-oxobutanal acetals and of 2-hydroxycyclobutanone ketals, J ORG CHEM, 64(14), 1999, pp. 5024-5028
Citations number
46
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
64
Issue
14
Year of publication
1999
Pages
5024 - 5028
Database
ISI
SICI code
0022-3263(19990709)64:14<5024:PSO4AA>2.0.ZU;2-#
Abstract
Irradiation of alpha,beta-unsaturated ketones (aliphatic, both open chain a nd 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 ca ses by bulb-to-bulb distillation). The resulting acetals were irradiated to give 2-hydroxycyclobutanone ketals, again through a simple procedure that gave a goad yield with open-chain aliphatic derivatives.