Reductive opening of 1H, 3H-benzo [de] isochromene: synthesis of 1, 8-difunctionalised naphthalenes

F Foubelo, B Moreno, M Yus

Index: Foubelo, Francisco; Moreno, Benjamin; Yus, Miguel Tetrahedron, 2004 , vol. 60, # 21 p. 4655 - 4662

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Citation Number: 17

Abstract

The lithiation of 1H, 3H-benzo [de] isochromene () with lithium and a catalytic amount of 4, 4′-di-tert-butylbiphenyl (DTBB, 5% molar) in THF at− 50° C gives dianionic intermediate, which by reaction with different electrophiles {H2O, D2O, tBuCHO, PhCHO, Me2CO,(CH3CH2) 2CO,[CH3 (CH2) 4] 2CO,(CH2) 5CO,(CH2) 7CO,(−)-menthone} at the same temperature followed by hydrolysis leads to functionalised alcohols. If after addition ...