Issue 29, 2012
From the journal:

Chemical Communications

Photochemical studies on aromatic γ,δ-epoxy ketones: efficient synthesis of benzocyclobutanones and indanones†

Yutian Shao,a   Chao Yang,a   Weijun Gui,a   Yang Liua  and  Wujiong Xia*ab  

* Corresponding authors

a State Key Lab of Urban Water Resource and Environment, The Academy of Fundamental and Interdisciplinary Sciences, Harbin Institute of Technology, Harbin 150080, China
E-mail: xiawj@hit.edu.cn
Fax: +86-451-86403760

b State Key Lab of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

Abstract

Irradiation of terminal aromatic γ,δ-epoxy ketones with a 450 W UV lamp led to Norrish type II cyclization/semi-pinacol rearrangement cascade reaction which formed the benzocyclobutanones containing a full-carbon quaternary center, whereas irradiation of substituted aromatic γ,δ-epoxy ketones led to the indanones through a photochemical epoxy rearrangement and 1,5-biradicals cyclization tandem reaction.

Graphical abstract: Photochemical studies on aromatic γ,δ-epoxy ketones: efficient synthesis of benzocyclobutanones and indanones

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Article information

DOI
https://doi.org/10.1039/C2CC17960A
Article type
Communication
Submitted
20 Dec 2011
Accepted
16 Feb 2012
First published
17 Feb 2012

Chem. Commun., 2012,48, 3560-3562

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Photochemical studies on aromatic γ,δ-epoxy ketones: efficient synthesis of benzocyclobutanones and indanones

Y. Shao, C. Yang, W. Gui, Y. Liu and W. Xia, Chem. Commun., 2012, 48, 3560 DOI: 10.1039/C2CC17960A

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