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Generation and Reactions of Lithiated tert ‐Butyl and 2,6‐Di( tert ‐butyl)‐4‐methylphenyl Cyclopropanecarboxylates
Author(s) -
Häner Robert,
Maetzke Thomas,
Seebach Dieter
Publication year - 1986
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19860690720
Subject(s) - chemistry , halide , alkyl , medicinal chemistry , tert butyl hydroperoxide , organic chemistry , catalysis
tert ‐Butyl and 2,6‐di( tert ‐butyl)‐4‐methylphenyl (BHT) cyclopropanecarboxylates ( 4 , 6 , 24 , 25 ) are lithiated with LiN(i‐Pr) 2 and t ‐BuLi, respectively. Reactions with alkyl halides, aldehydes, acyl chlorides, and heteroelectrophiles give α‐substituted BHT esters which can be cleaved ( t ‐BuOK/H 2 O/THF) to the corresponding carboxylic acids or reduced (LiAlH 4 /THF) to the cyclopropanemethanols.
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