Tetrahedron

DTBB-Catalysed dilithiation of styrene and its methyl-derivatives: introduction of two electrophilic reagents

M Yus, P Martı́nez, D Guijarro

Index: Yus, Miguel; Martinez, Pedro; Guijarro, David Tetrahedron, 2001 , vol. 57, # 51 p. 10119 - 10124

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Citation Number: 44

Abstract

The reaction of styrene and some methyl-substituted styrenes 1 with lithium and a catalytic amount of 4, 4′-di-tert-butylbiphenyl (DTBB) in the presence of several electrophiles [Me3SiCl, Me2CO, Et2CO,(CH2) 5CO, Pr2CO], in THF, at temperatures ranging from− 78 to 0° C, gave, after hydrolysis, products 2 resulting from addition of lithium to the olefinic double bond and successive trapping with the electrophilic reagent. When a carbonyl compound ...