Intramolecular carboxylate capture of an intermediate in aromatic electrophilic substitution. The 8,9,10,11-tetrahydro-7.11-methano-7H-cycloocta[de]naphthalene-9-endo-carboxylic acid system

Add time:09/09/2019    Source:sciencedirect.com

The α, α′-annelation of the enamine of 1,3-dihydro-2-phenalenone with methyl α-(bromomethyl)acrylate affords an aromatic bicyclic framework, methyl 8,9,10,11-tetrahydro-7,11-methano-12-keto-7H-cycloocta(de)-naphthalene-9-endo-carboxylate having the ester function positioned over the aromatic ring. The 9-exo-methyl-12, 12-dimethoxy ketal carboxylate anion derivative reacts with excess Br2 in aqueous solution affording the bromo lactone epoxide derived through capture of the intermediate of electorphilic attack on the naphthalene ring, 12, 12-dimethoxy-2, 3-endo-epoxy-11a-endo-hydroxy-1-exo, 4-dibromo-7, 11-methano-9-methyl-11a, 1, 2, 3, 4, 8, 9, 10, 11-octahydro-7 H-cycloocta [de] naphthalene-9-endo-carboxylic acid δ lactone.

We also recommend Trading Suppliers and Manufacturers of 3-BROMO-NAPHTHALENE-1-CARBOXYLIC ACID (cas 16726-66-2). Pls Click Website Link as below: cas 16726-66-2 suppliers

Prev:Original articleDecarboxylative bromination of α,β-unsaturated carboxylic acids via an anodic oxidation
Next:Carboxylic acid–pyridine supramolecular heterocatemer in a co-crystal)