Tetrahedron p. 865 - 872 (1984)
Update date:2022-08-03
Topics:
Cannone, P.
Caron, H.
Foscolos, G.
Reactions of 1,4-bis(bromomagnesio)butane and 1,5-bis(bromomagnesio)pentane with coumarin and 6-methylcoumarin gave a mixture of 1-(o-hydroxystyryl)cycloalkanol and 4-alkyl-3,4-dihydrocoumarin.A large difference in product distribution was observed between the two bifunctional reagents.Annelation was favored by the use of 1,4-bis(bromomagnesio)butane, whereas conjugate addition was observed with 1,5-bis(bromomagnesio)pentane and even in the use of 4-methylcoumarin.
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