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Updated: Aug 15, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Photochemical [2 + 2] cycloaddition reaction of carbonyl compounds with Danishefsky diene
Dian Agung Pangaribowo1, Manabu Abe2
1Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima, Hiroshima 739-8526, Japan. mabe@hiroshima-u.ac.jp and Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Jember, Jember, Jawa Timur 68121, Indonesia.
Abstract:
Danishefsky diene, trans-1-methoxy-3-trimethylsilyloxy-buta-1,3-diene, has been utilized in organic synthesis in thermal reactions for a long time. The purpose of this study is to investigate the photochemical reaction of ketones with Danishefsky diene. The [2 + 2] photocycloaddition products, oxetanes, were obtained in 65%-99% yield, along with the E to Z photochemical isomerisation of the diene. A mechanism involving intermediary triplet diradicals was proposed to rationalise the formation of the oxetanes.
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