Formation of macrocyclic lactones in the Paternò–Büchi dimerization reaction

J Arimura, T Mizuta, Y Hiraga…

Index: Arimura, Junya; Mizuta, Tsutomu; Hiraga, Yoshikazu; Abe, Manabu Beilstein Journal of Organic Chemistry, 2011 , vol. 7, p. 265 - 269

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Abstract

Abstract Furan-2-ylmethyl 2-oxoacetates 1a, b, in which the furan ring and the carbonyl moiety were embedded intramolecularly, were synthesized from commercially available furan-2-ylmethanol and their photochemical reaction (hν> 290 nm) was investigated. Twelve- membered macrocyclic lactones 2a, b with C i symmetry including two oxetane-rings, which are the Paternò–Büchi dimerization products, were isolated in ca. 20% yield. The ...

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