Internal Addition of Ketocarbenes to Conjugated Double Bonds
- 1 January 1972
- journal article
- research article
- Published by Wiley in Israel Journal of Chemistry
- Vol. 10 (2) , 375-383
- https://doi.org/10.1002/ijch.197200040
Abstract
The internal, copper‐catalysed, addition of keto‐carbenes (generated from a diazoketone group) to a double bond conjugated either to a ketone or carboxylic ester function has been found to be a feasible preparative reaction in selected cases. This, together with the facile and regiospecific hydrogenolysis of the resulting 1,2‐dicarbonyl cyclopropane intermediate, appear to constitute a convenient route to multifunctional bridged‐ring systems.Keywords
This publication has 28 references indexed in Scilit:
- Zur präparativen Chemie der DiazocarbonylverbindungenPublished by Springer Nature ,2006
- Asterane, II. Synthese und Hydrierung von Triasteran, Tetracyclo[3.3.1.02.8.04.6]nonanEuropean Journal of Inorganic Chemistry, 1967
- Reductive Opening of Conjugated Cyclopropyl Ketones with Lithium in Liquid Ammonia1The Journal of Organic Chemistry, 1966
- Intramolecular Reactions of Olefinic Diazo Ketones1The Journal of Organic Chemistry, 1966
- Perhydroindan Derivatives. V. The Synthesis of Some 3a-Substituted Derivatives1aThe Journal of Organic Chemistry, 1965
- Bridged Ring Systems by Anionic Rearrangement1Journal of the American Chemical Society, 1965
- Synthesis of tricyclic ketones by copper-catalyzed cyclization of monocyclic olefinic diazoketonesTetrahedron, 1965
- Reduction of Conjugated Cyclopropyl Ketones with Lithium in Liquid Ammonia.Acta Chemica Scandinavica, 1965
- A new synthesis of (±)-3-caroneTetrahedron, 1964
- INTRAMOLECULAR CYCLIZATION OF UNSATURATED DIAZOKETONESJournal of the American Chemical Society, 1961