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 svi 2020
Accepted
21 svi 2020
First published
21 svi 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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