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Paper | Special issue | Vol 77, No. 1, 2009, pp.389-400
Published online, 18th August, 2008
DOI: 10.3987/COM-08-S(F)31
Reaction of 1-Azabicyclo[1.1.0]butanes with 2,3-Dicyanofumarates; Interception of the Intermediate Zwitterions with Methanol

Grzegorz Mloston,* Malgorzata Celeda, Anthony Linden, and Heinz Heimgartner*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland


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.