Helvetica Chimica Acta

Lithium??und Kupfer??Derivate von α, α??doppeldeprotonierten Nitroalkanen.–Erzeugung, Eigenschaften und Umsetzungen mit Alkyl??und Allylhalogeniden

D Seebach, F Lehr

Index: Seebach,D.; Lehr,F. Helvetica Chimica Acta, 1979 , vol. 62, p. 2239 - 2257

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Citation Number: 24

Abstract

Summary Primary nitroalkanes are deprotonated twice in the a-position when treated with two mol-equiv. of butyllithium at-78" to-100" in THF containing HMPT to give dilithium derivatives 15 (the compound with R= C2H5 is stable up to-30"). The acidity of the nitronate proton of 13 is estimated to be in the same range as that of diisopropylamine. The C- nucleophilicity of the novel reagents 15 is dramatically increased as compared with that of ...