Photochemical release of aldehydes from alpha-acetoxy nitroveratryl ethers.
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]
Lage Robles
Jaime
J
Department of Chemistry, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg, Switzerland.
Bochet
Christian G
CG
D000080462:Acyclic Monoterpenes; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D039821:Monoterpenes / Q000138:chemical synthesis; D009574:Nitro Compounds / Q000737:chemistry*; D010777:Photochemistry; D013237:Stereoisomerism
D000080462:Acyclic Monoterpenes; D000447:Aldehydes; D004987:Ethers; D039821:Monoterpenes; D009574:Nitro Compounds; C108217:citronellal