1032129-68-2Relevant academic research and scientific papers
Photoaddition reactions of 1,2-diketones with silyl ketene acetals. Formation of β-hydroxy-γ-ketoesters
Dae, Won Cho,Lee, Hyang-Yeol,Sun, Wha Oh,Jung, Hei Choi,Hea, Jung Park,Mariano, Patrick S.,Ung, Chan Yoon
, p. 4539 - 4547 (2008/09/20)
(Chemical Equation Presented) Photochemical reactions taking place between 1,2-diketones and silyl ketene acetals and their excited state reaction mechanisms have been explored. Irradiation of benzene, acetone, or acetonitrile solutions containing 1,2-diketones and silyl ketene acetals is observed to promote formation of 1,4-dioxenes, resulting from [4 + 2]-cycloaddition, oxetanes, arising by Paterno-Buchi processes, and β-hydroxy-γ- ketoesters, generated by SET-promoted Claisen-type condensation. These competitive pathways leading from the excited states of the 1,2-diketones to these products are influenced by solvent polarity and the nature of the silyl ketene acetal and 1,2-diketone. The Claisen-type condensation process, following an SET desilylation pathway and predominating when the photoreactions are carried out in the polar solvent acetonitrile, represents an efficient method to prepare a variety of diversely substituted β-hydoxy-γ-ketoesters.
