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Title: The Preparation and Intramolecular Radical Cyclisation Reactions of Chiral Oxime Ethers
Authors: Booth, Susan E.
Jenkins, Paul R.
Swain, Christopher J.
First Published: 1998
Publisher: Sociedade Brasileira de Química, SBQ
Citation: Journal of the Brazilian Chemical Society 9(4), 389-395
Abstract: Chiral oxime ether 2 and Oxime ester 4 have been prepared by alkylation and esterification of the oxime 1. Racemic hydroxylamine 6 and chiral hydroxylamine 10 have been synthesised from N-hydroxysuccinimide and the corresponding alcohol in the presence of diethylazodicarboxylate, the two products were converted into the oxime ethers 7 and 11 respectively. The intramolecular radical cyclisation reactions of these oxime ethers and esters has been studied, successful reaction was observed to produce alkyl hydroxylamines 3, 8 and 12.
O éter-oxima quiral 2 e o éster-oxima 4 foram preparados para alquilação e esterificação da oxina 1. Hidroxiamina racêmica 6 e a hidroxiamina 10 foram sintetisadas a partir de N-hidroxipucanimida e o álcool correspondente na presença de di etil azodicarboxilato, e os dois produtos convertidos nos éteres-oximas 7 e 11 respectivamente. As reações de ciclização radicalar intramoleculares desses éteres e ésteres-oxima foram estudadas; a formação das alquil hidróxi-aminas 3, 8 e 12 foi observada nas reações bem sucedidas.
DOI Link: 10.1590/S0103-50531998000400012
ISSN: 0103-5053
eISSN: 1678-4790
Version: Publisher Version
Status: Peer-reviewed
Type: Journal Article
Rights: Creative Commons Attribution License (CC BY-NC 4.0)
Appears in Collections:Published Articles, Dept. of Chemistry

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