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David C. Harrowven, David D. Pascoe and Ian L. Guy Thermally Induced Cyclobutenone Rearrangements and Domino Reactions Angewandte Chemie International Edition 46

Version of Record online: 5 DEC 2006 | DOI: 10.1002/anie.200603538

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Four thermal-rearrangement pathways and a domino reaction leading to quinones arise from the thermolysis of cyclobutenones. The course of vinylcyclobutenone rearrangements is dictated by the nature of the substituent, R (see scheme): a cyclopentenone arises when R is an electron-rich alkene. In other cases thermolysis gives a cyclohexadienone, which may collapse with elimination to form a quinone, or tautomerize into a hydroquinone or cyclohexenedione.

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