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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.
1999
The Organic Chemistry/Polymer Science category includes resources concerned with the related fields of organic chemistry and polymer science. The organic chemistry resources deal with compounds of carbon with the exception of certain simple ones, such as the carbon oxides, carbonates, cyanides and cyanates (see Inorganic & Nuclear Chemistry). This category includes research on synthetic and natural organic compounds that may include other elements, such as hydrogen and oxygen, but also nitrogen, halogens, sulphur and phosphorous. Resources concerned with hydrocarbons, organic compounds containing only the elements carbon and hydrogen, are also included in this category. Examples are the alkanes, alkenes, alkynes and aromatics, such as benzene and naphthalene. Polymer science includes all resources dealing with the study, production and technology of polymers, which are compounds composed of very large molecules made up of repeating molecular units (monomers). Polymers may be natural substances, such as polysaccharides or proteins, or synthetic materials, such as nylon or polyethylene.
JOURNAL OF ORGANIC CHEMISTRY
sì
WOS:000081474300006
2-s2.0-0033067079
Sì, ma tipo non specificato
Inglese
Internazionale
STAMPA
64
5024
5028
SYNTHESIS; PHOTOCHEMISTRY
5
info:eu-repo/semantics/article
262
Manfrotto, C.; Mella, Mariella; Freccero, Mauro; Fagnoni, Maurizio; Albini, Angelo
1 Contributo su Rivista::1.1 Articolo in rivista
none
1.1 Articolo in rivista
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/132529
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