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Nucleophilic additions of sodium alkoxides to 4,4-dichloro-1,1-diphenyl- 2-azabuta-1,3-diene


Jacquot, S; Schmitt, G; Laude, B; Kubicki, M M; Blacque, Olivier (2000). Nucleophilic additions of sodium alkoxides to 4,4-dichloro-1,1-diphenyl- 2-azabuta-1,3-diene. European Journal of Organic Chemistry, (7):1235-1239.

Abstract

The reaction of some sodium alkoxides with 4,4-dichloro-1,1-diphenyl-2- azabuta-1,3-diene is described. Whereas sodium methoxide, ethoxide or isopropoxide leads to 1,3-bis(alkoxy)- and/or 1,3,4-tris(alkoxy)-2-azabut-2- enes, the sodium salt of ethyl glycolate gives a Δ2-oxazoline. Mechanisms for the formation of these products are proposed.

Abstract

The reaction of some sodium alkoxides with 4,4-dichloro-1,1-diphenyl-2- azabuta-1,3-diene is described. Whereas sodium methoxide, ethoxide or isopropoxide leads to 1,3-bis(alkoxy)- and/or 1,3,4-tris(alkoxy)-2-azabut-2- enes, the sodium salt of ethyl glycolate gives a Δ2-oxazoline. Mechanisms for the formation of these products are proposed.

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Language:English
Date:2000
Deposited On:11 Nov 2022 13:25
Last Modified:27 Jun 2024 01:41
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:1099-0690
Additional Information:cited By 9
OA Status:Closed
Publisher DOI:https://doi.org/10.1002/1099-0690(200004)2000:7<1235::AID-EJOC1235>3.0.CO;2-8
Related URLs:https://www.scopus.com/inward/record.uri?eid=2-s2.0-0034009841&doi=10.1002%2f1099-0690%28200004%292000%3a7%3c1235%3a%3aAID-EJOC1235%3e3.0.CO%3b2-8&partnerID=40&md5=6c26ffb8f163d5092d72b7db6050f5ad