Photochemistry of (‐)‐Levoglucosenone: Norrish Type I Reaction and Photoinduced Electron Transfer Processes
Year: 2026
Type: article
Abstract: Photochemical reactions of levoglucosenone (LGO) considerably extend its potential as a synthon in organic synthesis. At the photochemical excited state, LGO undergoes a reaction that resembles Norrish type I reactions. Ketene intermediates are formed and trapped with alcohols or amines. A variety of alkenes with interesting substitution patterns are thus obtained. The reaction mechanism has been determined and compared to the classical mechanism of the Norrish type I reaction of Cyrene. The triplet energies of both compounds have also been determined by phosphorescence at low temperature. In the case of photochemically excited LGO, electron transfer from tertiary aromatic amines is possible. Such a photochemical electron transfer can also be induced by sensitization involving triplet energy transfer from a sensitizer to LGO. These processes are competitive with the efficient Norrish type I reactions. In such reactions, the bicyclic structure of LGO is conserved, and aniline derivatives are stereospecifically added.
Source: ChemPhotoChem
DOI: 10.1002/cptc.70171
Institutions: Centre National de la Recherche Scientifique, Institut de Physique et Chimie des Matériaux de Strasbourg, Université de Strasbourg, Université Paris-Saclay, Biomolécules : Conception, Isolement, Synthèse, Université Paris Cité, Interfaces Traitements Organisation et Dynamique des Systèmes, Université de Reims Champagne-Ardenne, AgroParisTech, Agro-Biotechnologies Industrielles, Hiroshima University
Language: English
Subfield: Physical and Theoretical Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,030
OpenAlex ID: W7160014995