Abstract
The kinetics of the photochemical Norrish-Yang reaction in single crystals was studied using the example of 1,3,5,7-tetraazatricyclo[3.3.1.13,7]decane 4-(2,4,6-triisopropylbenzoyl)benzoate by X-ray...
Highlights
During the Norrish-Yang reaction an achiral reactant molecule transforms into a chiral photoproduct molecule
Since the Norrish-Yang reaction in a crystalline state can be conducted in a more controlled manner than in solution, it attracts the interest of many organic chemists.[1−8] Its advantage over reactions conducted in solutions is mainly connected with the possibility to correlate chemical behavior with a crystal structure
It is worth adding that the reaction in a crystalline state can proceed differently than in solutions owing to different geometrical parameters for both media
Summary
During the Norrish-Yang reaction an achiral reactant molecule transforms into a chiral photoproduct molecule. The analysis of parameter d only enabled the rationalization of photochemical reactivity in crystals, as it was in the case of the Yang cyclization of α-1-norbornylacetophenone derivatives.[2,8] The analysis of d and Δ explained the predominant formation of a five-membered ring (not fourmembered) for phenylethaneaminium 4-(2,4,6triisopropylbenzoyl)benzoate.[7]. According to the topochemical postulate, a photochemical reaction proceeds in crystals when there is the possibility of breaking old bonds and forming new ones Such a reaction is easier when the required atomic shifts are small and a reaction cavity[21−27] does not significantly change its geometry.[28,29] when there is free space close to the reacting molecular fragments, the reaction can occur, the necessary shifts and changes are significant. For a comparison of the spectra, the intensities of the bands were normalized in relation to the band at 1600 cm−1 resulting from a CC aromatic ring stretching mode
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