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Photochimie en solution. XXIV. Mecanisme de l'addition des aldehydes aux double liaisons ethyleniques activees par des groupements attracteurs d'electrons
Kawenoki, Isabelle,Maurel, Daniele,Kossanyi, Jean
, p. 385 - 390 (2007/10/02)
The mechanism of the photochemical addition of aliphatic aldehydes to electron-deficient olefins has been rationalized.No addition to α,β-unsaturated ketones was observed when the latter were excited.The reaction can be explained by a first self-quenching step of the aliphatic aldehyde involving its lowest triplet state, which is reached with a moderate quantum yield (0.5).The radical R-C.=O produced in the self quenching process adds to the olefin at the more positively-charged carbon atom.The reaction ends by a hydrogen atom exchange between the radical produced by this addition and the radical R-C.HOH.The quantum yield of the product formation is much higher with benzaldehyde owing to the almost unity value of the intersystem crossing, but it competes with the formation of benzile.
