Issue 26, 2020

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

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

Supplementary files

Article information

Article type
Paper
Submitted
03 5 2020
Accepted
21 5 2020
First published
21 5 2020

Org. Biomol. Chem., 2020,18, 4962-4970

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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