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Alkylation and aldol reactions of aldoxime anions
Author(s) -
Hassner Alfred,
Näumann Fritz
Publication year - 1988
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19881211021
Subject(s) - chemistry , alkylation , carbanion , oxime , aldol condensation , deprotonation , medicinal chemistry , silylation , aldol reaction , organic chemistry , protonation , stereochemistry , catalysis , ion
The reaction of Z aldoximes with BuLi to give dianions and the properties of the latter were examined. D‐Labelling and silylation confirm previous findings that only the Z isomer forms the dianion. Z ‐Hexanal oxime and Z ‐octanal oxime were deprotonated with BuLi, and the anions underwent aldol condensation reactions with several aldehydes and ketones including α,β‐unsaturated aldehydes. Attempts to alkylate monoanions of OTHP ethers of aldoximes failed. However, carbanion addition to the CN bond of some oxime OTHP ethers was observed.