Tetrahedron

Arene-catalysed lithiation of phenyl-and 1, 1-diphenylcyclopropane: synthetic applications

C Gómez, VJ Lillo, M Yus

Index: Gomez, Cecilia; Lillo, Victor J.; Yus, Miguel Tetrahedron, 2007 , vol. 63, # 22 p. 4655 - 4662

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Citation Number: 4

Abstract

The reaction of phenylcyclopropane (1) with an excess of lithium and a catalytic amount of DTBB (2.5% molar) in THF at room temperature, followed by treatment with an electrophile [Me3SiCl, PhMe2SiCl, t-BuCHO, PhCHO, Me2CO, Et2CO,(CH2) 5CO, adamantan-2-one, i- Pr2CO, di (cyclopropyl) ketone] and final hydrolysis with water leads to allylic products 10 or 11 depending on the structure of the electrophile: whereas for chlorosilanes or crowded ...

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