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Reaction of 1-azabicyclo[1.1.0]butanes with 2,3-dicyanofumarates; interception of the intermediate zwitterions with methanol


Mloston, G; Celeda, M; Linden, A; Heimgartner, H (2009). Reaction of 1-azabicyclo[1.1.0]butanes with 2,3-dicyanofumarates; interception of the intermediate zwitterions with methanol. Heterocycles, 77(1):389-400.

Abstract

The reaction of 3-phenyl-1-azabicyclo[1.1.0]butane (1c) with 2,3-dicyanofumarates ((E)-5) in dichloromethane at room temperature yields mixtures of cis- and trans-2,3-dicyano-4-phenyl-1-azabicyclo[2.1.1]hexane- 2,3-dicarboxylates (cis,trans-4). The proposed two-step reaction mechanism via a zwitterionic intermediate of type (6) is supported by trapping experiments with methanol: when the reactions of 1-azabicyclo[1.1.0]butanes (1) with dimethyl 2,3-dicyanofumarate ((E)-5a) are carried out in methanol, dimethyl (E)-2-(azetidin-1-yl)-3-cyanobut-2-enedioates (7) are formed as the only products.

Abstract

The reaction of 3-phenyl-1-azabicyclo[1.1.0]butane (1c) with 2,3-dicyanofumarates ((E)-5) in dichloromethane at room temperature yields mixtures of cis- and trans-2,3-dicyano-4-phenyl-1-azabicyclo[2.1.1]hexane- 2,3-dicarboxylates (cis,trans-4). The proposed two-step reaction mechanism via a zwitterionic intermediate of type (6) is supported by trapping experiments with methanol: when the reactions of 1-azabicyclo[1.1.0]butanes (1) with dimethyl 2,3-dicyanofumarate ((E)-5a) are carried out in methanol, dimethyl (E)-2-(azetidin-1-yl)-3-cyanobut-2-enedioates (7) are formed as the only products.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:January 2009
Deposited On:14 Mar 2009 15:30
Last Modified:05 Apr 2016 12:57
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Rector of the University of Łodz, F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.3987/COM-08-S(F)31

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