The First Ring-Enlargement of a 1-Azabicyclo[1.1.0]butane to a 1-Azabicyclo[2.1.1]hexane

The First Ring-Enlargement of a 1-Azabicyclo[1.1.0]butane to a 1-Azabicyclo[2.1.1]hexane

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 cycloaddi...

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Veröffentlicht in:Helvetica chimica acta 2006-03, Vol.89 (3), p.442-449
Hauptverfasser: Mlostoń, Grzegorz, Heimgartner, Heinz
Format: Artikel
Sprache:eng
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1-Azabicyclo[1.1.0]butanes
1-Azabicyclo[2.1.1]hexanes
Cycloadditions
Ring-enlargement reactions
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Heimgartner, Heinz
description 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).
doi_str_mv 10.1002/hlca.200690044
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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).</description><subject>1-Azabicyclo[1.1.0]butanes</subject><subject>1-Azabicyclo[2.1.1]hexanes</subject><subject>Cycloadditions</subject><subject>Ring-enlargement reactions</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNqFkE9PwjAYhxujiYhePe8LdL79s3Y94gJiQhANBhJDmq7rYDo2s84IfnohGGK8eHoPz_v8Dg9C1wRCAkBvVqU1IQUQCoDzE9QhEaWYChmdog4AiTEQNT9HF96_AoBSIDtoPl25YFA0vg2eimqJ-1VpmqVbu6oN6jwwAcG9L5MWdmvL-oWEJIRF-tGaygVt_RfTHSaLldvs8CU6y03p3dXP7aLnQX-aDPHo4e4-6Y2wZUJy7KgQErIoYxFnVKWcERNZl8c2y6QQNANHbJSrWMSpA2FykzouVZyqmBNKCeui8LBrm9r7xuX6vSnWptlqAnrfRe-76GOXnaAOwmdRuu0_33o4Snq_XXxwC9-6zdE1zZsWkslIz8Z3enw7mSWPcqIZ-wZ6R3QY</recordid><startdate>200603</startdate><enddate>200603</enddate><creator>Mlostoń, Grzegorz</creator><creator>Heimgartner, Heinz</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>200603</creationdate><title>The First Ring-Enlargement of a 1-Azabicyclo[1.1.0]butane to a 1-Azabicyclo[2.1.1]hexane</title><author>Mlostoń, Grzegorz ; Heimgartner, Heinz</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3674-e26670d5d354329b431a5cef8cdd7662d0e1c5f9868be06afabe4798b98412213</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>1-Azabicyclo[1.1.0]butanes</topic><topic>1-Azabicyclo[2.1.1]hexanes</topic><topic>Cycloadditions</topic><topic>Ring-enlargement reactions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mlostoń, Grzegorz</creatorcontrib><creatorcontrib>Heimgartner, Heinz</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Helvetica chimica acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mlostoń, Grzegorz</au><au>Heimgartner, Heinz</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The First Ring-Enlargement of a 1-Azabicyclo[1.1.0]butane to a 1-Azabicyclo[2.1.1]hexane</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>2006-03</date><risdate>2006</risdate><volume>89</volume><issue>3</issue><spage>442</spage><epage>449</epage><pages>442-449</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><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). 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subjects 1-Azabicyclo[1.1.0]butanes
1-Azabicyclo[2.1.1]hexanes
Cycloadditions
Ring-enlargement reactions
title The First Ring-Enlargement of a 1-Azabicyclo[1.1.0]butane to a 1-Azabicyclo[2.1.1]hexane
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