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Selektive Synthesen mit Organometallen V : Trimethylsilylmethyl‐kalium und andere Spitzenkönner unter den Metallierungsmitteln
Author(s) -
Hartmann Jürgen,
Schlosser Manfred
Publication year - 1976
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.19760590212
Subject(s) - chemistry , cyclopropane , butyllithium , allylic rearrangement , potassium , reagent , medicinal chemistry , organic chemistry , catalysis , ring (chemistry)
Trimethylsilylmethylpotassium and other outstanding metallating agents. For the metallation of allylic and benzylic positions, trimethylsilylmethylpotassium is the most powerful reagent. Butyllithium in the presence of potassium t ‐butoxide however, can usually replace it. Olefinic and cyclopropane hydrogen atoms are most readily attacked by pentylsodium, especially if the reaction is carried out in presence of potassium t ‐butoxide. Trimethylsilylmethylpotassium, however, will equally work if an activating group, such as methoxy, is present in the substrate. Generalisations concerning the metallation mechanisms are drawn.