Issue 34, 2020

Spiro 1,3-indandiones: intramolecular photochemical reactions of carbonyl groups with carbon–carbon double bonds

Abstract

2-Substituted 1,3-indandione derivatives are known to undergo a photochemical rearrangement into phthalides. We find that in the presence of a substituent involving a double carbon–carbon bond in the vicinity of the carbonyl group in spiro-1,3-indandiones, a variety of other types of intramolecular photochemical reactions readily occur: 1,3-acyl shift, intramolecular reversible Paternò–Büchi reaction, and formal oxa-[4+2]-cycloaddition. A specific feature of these reactions of spiro-1,3-indandiones is their photo-reversibility. The structures of polycyclic products of these reactions were determined spectroscopically and, in most cases, by single crystal X-ray structure determinations. A number of the products, especially those involving benzazulene or oxatricyclo[4.2.1.03,8]nonane moieties are synthetic analogues of natural compounds of interest owing to a variety of their biological activities.

Graphical abstract: Spiro 1,3-indandiones: intramolecular photochemical reactions of carbonyl groups with carbon–carbon double bonds

Supplementary files

Article information

Article type
Paper
Submitted
10 Jun 2020
Accepted
24 Jul 2020
First published
30 Jul 2020

New J. Chem., 2020,44, 14373-14378

Spiro 1,3-indandiones: intramolecular photochemical reactions of carbonyl groups with carbon–carbon double bonds

V. Lokshin, H. Clavier and V. Khodorkovsky, New J. Chem., 2020, 44, 14373 DOI: 10.1039/D0NJ02923H

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