Term: oxa-di-π-methane rearrangement https://doi.org/10.1351/goldbook.O04359 Definition: A photochemical reaction of a β,γ-unsaturated ketone to form a saturated α-cyclopropyl ketone. The rearrangement formally amounts to a 1,2-acyl shift and 'bond formation' between the former α and γ carbon atoms. O04359.png Related Terms: 1) di-π-methane rearrangement (http://doi.org/10.1351/goldbook.D01745). 2) photochemical reaction (http://doi.org/10.1351/goldbook.P04585). 3) rearrangement (http://doi.org/10.1351/goldbook.R05194). Image: Not defined (https://goldbook.iupac.org/img/inline/O04359.png) Source: PAC, 1996, 68, 2223. 'Glossary of terms used in photochemistry (IUPAC Recommendations 1996)' on page 2258 (https://doi.org/10.1351/pac199668122223) Citation: 'oxa-di-π-methane rearrangement' in IUPAC Compendium of Chemical Terminology, 5th ed. International Union of Pure and Applied Chemistry; 2025. Online version 5.0.0, 2025. https://doi.org/10.1351/goldbook.O04359 License: The IUPAC Gold Book is licensed under Creative Commons Attribution-ShareAlike CC BY-SA 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) for individual terms. Disclaimer: The International Union of Pure and Applied Chemistry (IUPAC) is continuously reviewing and, where needed, updating terms in the Compendium of Chemical Terminology (the IUPAC Gold Book). Users of these terms are encouraged to include the version of a term with its use and to check regularly for updates to term definitions that you are using.