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Temperature and Viscosity Dependence of the Spin‐Directed Stereoselectivity of the Carbonyl–Alkene Photocycloaddition
Author(s) -
Griesbeck Axel G.,
Bondock Samir,
Gudipati Murthy S.
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20011217)40:24<4684::aid-anie4684>3.0.co;2-9
Subject(s) - stereoselectivity , alkene , oxetane , singlet state , chemistry , selectivity , photochemistry , excited state , triplet state , product distribution , multiplicity (mathematics) , polymer chemistry , organic chemistry , molecule , catalysis , physics , mathematical analysis , mathematics , nuclear physics
The multiplicity of the excited state controls the product distribution in the formation of endo / exo ‐oxetane 3 in the photocycloaddition of aldehydes 1 (R = Ph, Et, Me, i Bu) with dihydrofuran 2 (Paternò–Büchi reaction). Whether the singlet or triplet channel dominates is strongly dependent on the temperature, which is therefore critical for the selectivity of the reaction.