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月 2020
Accepted
21 5月 2020
First published
21 5月 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements