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The first ring-enlargement of a 1-Azabicyclo[1.1.0]butane to a 1-Azabicyclo[2.1.1]hexane


Mloston, G; Heimgartner, H (2006). The first ring-enlargement of a 1-Azabicyclo[1.1.0]butane to a 1-Azabicyclo[2.1.1]hexane. Helvetica Chimica Acta, 89(3):442-449.

Abstract

The reactions of 3-phenyl-1-azabicyclo[1.1.0]butane (4) with dimethyl dicyanofumarate ((E)-8) and dimethyl dicyanomaleate ((Z)-8) lead to the same mixture of cis- and trans-4-phenyl-1-azabicyclo[2.1.1]-hexane 2,3-dicarboxylates (cis-11 and trans-11, resp.; Scheme 3). This result of a formal cycloaddition to the central C-N bond of 4 is interpreted by a stepwise reaction mechanism via a relatively stable zwitterionic intermediate 10, which could be intercepted by morpholine to give a 1 : 1 : 1 adduct 12, which undergoes a spontaneous elimination of HCN to yield the fumarate 13 (Scheme 4).

Abstract

The reactions of 3-phenyl-1-azabicyclo[1.1.0]butane (4) with dimethyl dicyanofumarate ((E)-8) and dimethyl dicyanomaleate ((Z)-8) lead to the same mixture of cis- and trans-4-phenyl-1-azabicyclo[2.1.1]-hexane 2,3-dicarboxylates (cis-11 and trans-11, resp.; Scheme 3). This result of a formal cycloaddition to the central C-N bond of 4 is interpreted by a stepwise reaction mechanism via a relatively stable zwitterionic intermediate 10, which could be intercepted by morpholine to give a 1 : 1 : 1 adduct 12, which undergoes a spontaneous elimination of HCN to yield the fumarate 13 (Scheme 4).

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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:2006
Deposited On:22 May 2012 06:53
Last Modified:07 Dec 2017 11:05
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:University of Łódz´ (Grant No. 505/683), F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.200690044

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