Studies on intramolecular alkylation. V. Intramolecular alkylation of the aromatic ring in tetrahydronaphthyl diazomethyl ketones

Abstract

The acid-catalysed reactions in weakly nucleophilic environments of 2-diazoacetyl-l,2,3,4-tetrahydronaphthalene (ll), of 6-diazoacetyl-5,6,7,8-tetrahydro-2-naphthol (2), of 6-diazoacetyl-5,6,7,8- tetrahydro-2-naphthyl methyl ether (3) and its 2,8 and 2,5 isomers (14) and (17), and of 6-diazo- acetyl-5,6,7,8-tetrahydro-6-trifluoroacetoxy-2-naphthyl methyl ether (9) have been studied. Several of the spirocyclohexa-2,5-dienone derivatives prepared thus, (4), (8) and (16), provide potential intermediates or models for the synthesis of tetracyclic diterpenoids.