Synthesis of Isocomene (Pirrung)

7 Dezembro 2016, 14:00 • Christopher David Maycock

1,3-diones and their alkylation. Preparation of 2-methylcyclohexane-1,3-dione. Formation of a vinyl ether by an addition elimination reaction or via substitution of a chloride. Methods for the remote alkylation of 1,3-diones and beta-ketoesters. alfa-Alkylations of ketones in general. Reaction of alf-beta-unsaturated ketones with organometallic reagents (1,2- versus 1,4-addition) Use of copper reagents for 1,4-additions.1,2-additions with Mg reagents. Acid hydrolysis of vinyl ethers and elimination of water from beta-hydroxyketones. Intramolecular [2+2]-cycloadditions using UV-light. Conformation of transition states and the stereochemical outcome of reactions.