Stereoselectivity of the Hydrogen‐Atom Transfer in Benzophenone–Tyrosine Dyads: An Intramolecular Kinetic Solvent Effect

To be or not to be solvated is the decisive parameter that controls the photoinduced hydrogen‐atom transfer in diastereomeric ketone/phenol dyads. A kinetic solvent effect that refers to hydrogen bonding between the phenol and the solvent is suggested to be the main source of the stereoselective dis...

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Bibliographic Details
Published in:Chemistry : a European journal 2009-03, Vol.15 (13), p.3061-3064
Main Authors: Hörner, Gerald, Hug, Gordon L., Lewandowska, Anna, Kazmierczak, Franciszek, Marciniak, Bronislaw
Format: Article
Language:English
Subjects:
Benzophenones - chemistry
biradicals
Hydrogen Bonding
hydrogen bonds
Ketones
Kinetics
Molecular Structure
Photochemistry
solvent effects
Solvents - chemistry
Stereoisomerism
Tyrosine - chemistry
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Summary:To be or not to be solvated is the decisive parameter that controls the photoinduced hydrogen‐atom transfer in diastereomeric ketone/phenol dyads. A kinetic solvent effect that refers to hydrogen bonding between the phenol and the solvent is suggested to be the main source of the stereoselective discrimination in the hydrogen transfer (see figure). To be or not to be solvated is the decisive parameter that controls the photoinduced hydrogen‐atom transfer in diastereomeric ketone/phenol dyads. A kinetic solvent effect that refers to hydrogen bonding between the phenol and the solvent is suggested to be the main source of the stereoselective discrimination in the hydrogen transfer (see figure).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200802674