Alkylation and aldol reactions of aldoxime anions

Alfred Hassner; Fritz Näumann

doi:10.1002/cber.19881211021

Alkylation and aldol reactions of aldoxime anions

Alfred Hassner, Fritz Näumann

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

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Abstract

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 CN bond of some oxime OTHP ethers was observed.

Original language	English
Pages (from-to)	1823-1826
Number of pages	4
Journal	Chemische Berichte
Volume	121
Issue number	10
DOIs	https://doi.org/10.1002/cber.19881211021
State	Published - 1988

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abstract = "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 CN bond of some oxime OTHP ethers was observed.",

author = "Alfred Hassner and Fritz N{\"a}umann",

year = "1988",

doi = "10.1002/cber.19881211021",

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AU - Hassner, Alfred

AU - Näumann, Fritz

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N2 - 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 CN bond of some oxime OTHP ethers was observed.

AB - 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 CN bond of some oxime OTHP ethers was observed.

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Alkylation and aldol reactions of aldoxime anions

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