Photochemical Release of Aldehydes from α-Acetoxy Nitroveratryl Ethers
- 13 July 2005
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (16), 3545-3547
- https://doi.org/10.1021/ol051280w
Abstract
Photolabile aldehyde-releasing precursors (alpha-acetoxy ethers) were prepared by reduction of the corresponding esters with DIBAL and quenching the intermediate aluminum hemiacetal with acetic anhydride. These species smoothly released aldehydes upon irradiation with UV light at 350 nm. Using this method, not only simple model aliphatic aldehydes were liberated but also specimens relevant for the flavor and fragrance industry (methional, phenylacetaldehyde, and (R)-citronellal). [reaction: see text]Keywords
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