Aromatic aldols and 1,5-diketones as optimized fragrance photocagesThis paper is part of a themed issue on photoremovable protecting groups: development and applications

Aromatic aldols and 1,5-diketones with abstractable -hydrogen atoms are highly photoactive cage molecules for the release of fragrance carbonyl compounds (aldehydes and Michael ketones, respectively). Aldols 3ad 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 -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. Aromatic aldols and 1,5-diketones with abstractable -hydrogen atoms are highly photoactive cage molecules for the release of fragrance compounds (aldehydes and Michael ketones, respectively). By tuning the properties of the chromophores, -damascone cages were developed for selective release of fragrances under air and solar irradiation. The intermediates of the Norrish II process were observed by laser transient absorption spectroscopy.