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DOI: 10.1055/s-2001-15059
New Results on the Triplet Photoreactivity of β,γ-Unsaturated Aldehydes: Diastereoselective Synthesis of Cyclopropanecarbaldehydes
Publication History
Publication Date:
24 September 2004 (online)
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Abstract
A comparative study on the triplet photoreactivity of a series of β,γ-unsaturated aldehydes and methyl ketones has been carried out. Aldehydes 14 and 20 were found to undergo the oxa-di-p-methane rearrangement yielding the corresponding cyclopropane carbaldehydes 15 and 21 diastereoselectively. Decarbonylations and 1,3-carbonyl migrations have been observed in some cases, although these reactions do not take place via a Norrish Type I mechanism.
Keywords
β,γ-unsaturated carbonyl compounds - oxa-di-p-methane rearrangement - decarbonylation - cyclopropanecarbaldehydes - 1,3-formyl migration.
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References
Aldehydes 15a-b and 21a-d undergo spontaneous oxidation in the presence of atmospheric oxygen. The combustion analyses quoted correspond to the carboxylic acids resulting from oxidation.