1987
DOI: 10.1002/chin.198708158
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ChemInform Abstract: Generation and Reactions of Lithiated tert. Butyl and 2,6‐Di(tert‐butyl)‐4‐methylphenyl Cyclopropane Carboxylates.

Abstract: (14.VI1.86) trrf-Butyl and 2,6-di(tert-butyl)-4-methylphenyl (RHT) cyclopropanecarboxylates (4, 6, 24, 25) are lithiated with LiN(i-Pr), and t -BuLi, respectively. Reactions with alkyl halides, aldehydes, acyl chlorides, and heteroelectrophiles give a-substituted BHT esters which can be cleaved (t-BuOK/H,O/THF) to the corresponding carboxylic acids or reduced (LiAIH,/THF) to the cyclopropdnemethanols.Though cyclopropane (la) itself is more acidic than the less strained cycloalkanes and open-chain alkanes (cf. … Show more

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