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Issue 26, 2020
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Photochemical [2 + 2] cycloaddition reaction of carbonyl compounds with Danishefsky diene

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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.

Graphical abstract: Photochemical [2 + 2] cycloaddition reaction of carbonyl compounds with Danishefsky diene

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Supplementary files

Article information


Submitted
03 May 2020
Accepted
21 May 2020
First published
21 May 2020

Org. Biomol. Chem., 2020,18, 4962-4970
Article type
Paper

Photochemical [2 + 2] cycloaddition reaction of carbonyl compounds with Danishefsky diene

D. A. Pangaribowo and M. Abe, Org. Biomol. Chem., 2020, 18, 4962
DOI: 10.1039/D0OB00921K

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