De Mayo reaction
The de Mayo reaction is a name reaction in organic chemistry and named after Paul Jose de Mayo (1924–1994). In this reaction, a 1,5-diketone can be obtained by photochemical reaction of an alkene with an enolizable 1,3-diketone . The reaction is classified as a domino reaction .
mechanism
The enolizable 1,3-diketone 1 reacts with an alkene in a [2 + 2] cycloaddition. A β-hydroxy ketone 3 is formed . This reaction step is followed by a retro-aldol reaction, which leads to the opening of the cyclobutane ring 3 . A 1,5-diketo compound 5 is formed mechanistically via a keto-enol equilibrium .
literature
- P. de Mayo, H. Takeshita, ABM A Sattar: The Photochemical Synthesis of 1,5-Diketones and their Cyclization. A New Annulation Process. In: Proceedings of the Chemical Society . 1962, p. 119, doi : 10.1039 / PS9620000097 .
- Paul de Mayo: Enone photoannelation. In: Accounts of Chemical Research. 4, No. 2, 1971, pp. 41-47, doi : 10.1021 / ar50038a001 .
- JJ Li: Name Reactions. A Collection of Detailed Reaction Mechanisms . Springer, 2009, ISBN 978-3-642-01052-1 , p. 173.
Individual evidence
- ↑ on Paul Jose de Mayo see: James F. King, Karl Overton: Paul Jose De Mayo. August 8, 1924 - July 26, 1994 Elected FRS 1975. In: Biographical Memoirs of Fellows of the Royal Society. 45, 1999, pp. 111-128, doi : 10.1098 / rsbm.1999.0009 .
- ^ László Kürti , Barbara Czakó: Strategic Applications of Named Reactions in Organic Synthesis . Elsevier Academic Press, Burlington / San Diego / London 2005, ISBN 0-12-369483-3 .