Tetrahedron

Cyclopropylmethyl-and cyclobutylmethyllithium by an arene-catalyzed lithiation. Stability and reactivity

I Peñafiel, IM Pastor, M Yus

Index: Penafiel, Itziar; Pastor, Isidro M.; Yus, Miguel Tetrahedron, 2010 , vol. 66, # 16 p. 2928 - 2935

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Citation Number: 7

Abstract

The reaction of (chloromethyl) cyclopropane 5 and (bromomethyl) cyclobutane 8 with lithium and a substoichiometric amount of DTBB, in the presence of different carbonyl compounds as electrophiles, in THF at− 78° C leads, after hydrolysis, to the corresponding cycloalkyl alcohols 6 and 9, respectively. However, when the same starting materials are lithiated using naphthalene as catalyst in diethyl ether and at higher temperature (0 or 25° C), and ...

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