Reactions of 1,2-Naphthoquinones with Allyltrialkyltins

Article abstract of DOI:10.1021/jo00185a003

BF3-mediated allylation of 1,2-naphthoquinone and its 3-substituted derivatives with allyl-, (2-methyl-2-propenyl)-, trans-2-butenyl-, and (3-methyl-2-butenyl)trialkyltin afforded selectively the corresponding 4-allyl-1,2-naphthalenediols, which were isolated as diacetate or quinone.In the reactions with trans-2-butenyltributyltin, the regioisomer ratio of the α- vs. γ-adduct depends on the nature of substituents in position 3 of quinones.The reactions with (3-methyl-2-butenyl)tributyltin afforded α-adducts exclusively.Whether the reactions proceed toward 1,2-addition or 1,4-addition depends both on the electronic characteristics of the substituents and on the bulkiness of allyl moieties.