Aromatic aldols and 1,5-diketones as optimized fragrance photocages.
Aromatic aldols and 1,5-diketones with abstractable γ-hydrogen atoms are highly photoactive cage molecules for the release of fragrance carbonyl compounds (aldehydes and Michael ketones, respectively). Aldols 3a-d are easily accessible by Mukaiyama addition and are cleaved to form the substrates with high quantum yields under solar radiation. By tuning the properties of the chromophores, a series of δ-damascone cages 5 were developed that can be used for selective and fast (5a,e) or slow (5b,d) release of fragrances under air and solar irradiation. The intermediates of the Norrish II process were observed by laser transient absorption spectroscopy.
Department of Chemistry, University of Cologne, Köln, Germany. griesbeck@uni-koeln.de
Axel G
AG
Griesbeck
Olga
O
Hinze
Helmut
H
Görner
Ursula
U
Huchel
Christian
C
Kropf
Uta
U
Sundermeier
Thomas
T
Gerke
D000447:Aldehydes / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010782:Photolysis
D000447:Aldehydes; D007659:Ketones