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Issue 10, 2009
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Synthesis of γ-lactols, γ-lactones and 1,4-monoprotected succinaldehydes under moderately concentrated sunlight

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Abstract

The usefulness of solar light for carrying out photocatalytic reactions involving the formation of a carbon–carbon bond has been explored. Thus, some radical alkylations of α,β-unsaturated acids or aldehydes have been carried out in a mixed aqueous solution. Under these conditions, alkyl radicals are generated from i-PrOH and 1,3-dioxolane by photocatalyzed hydrogen abstraction. A water soluble photocatalyst (disodium benzophenondisulfonate, BPSS) was used, which greatly simplifies work up. With reasonably efficient radical traps (e.g. maleic acid), the syntheses could be carried out up to completion on a 10 gram scale within 10–15 hours exposure to sunlight in a solar concentrator (SOLFIN apparatus) in November in Almeria (Spain). The alkylation of some α,β-unsaturated aldehydes have been likewise performed under the same conditions.

Graphical abstract: Synthesis of γ-lactols, γ-lactones and 1,4-monoprotected succinaldehydes under moderately concentrated sunlight

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Article information


Submitted
04 Mar 2009
Accepted
15 Jul 2009
First published
04 Aug 2009

Green Chem., 2009,11, 1653-1659
Article type
Paper

Synthesis of γ-lactols, γ-lactones and 1,4-monoprotected succinaldehydes under moderately concentrated sunlight

D. Dondi, S. Protti, A. Albini, S. M. Carpio and M. Fagnoni, Green Chem., 2009, 11, 1653
DOI: 10.1039/B904427B

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