PittsburghV1, PubMed, Corpus, bibRecord, 000967

Rearrangement reactions of 1,1-divinyl-2-phenylcyclopropanes.

Identifieur interne : 000967 ( PubMed/Corpus ); précédent : 000966; suivant : 000968

Rearrangement reactions of 1,1-divinyl-2-phenylcyclopropanes.

Auteurs : E Ben Hay ; Hanmo Zhang ; Dennis P. Curran

Source :

Journal of the American Chemical Society [ 1520-5126 ] ; 2015.

RBID : pubmed:25530073

English descriptors

KwdEn :
- Acids (chemistry), Amides (chemistry), Cyclization, Cyclopropanes (chemistry), Esters (chemistry), Free Radicals (chemical synthesis), Free Radicals (chemistry), Molecular Structure, Temperature, Vinyl Compounds (chemistry).
MESH :
- chemical , chemical synthesis : Free Radicals.
- chemical , chemistry : Acids, Amides, Cyclopropanes, Esters, Free Radicals, Vinyl Compounds.
- Cyclization, Molecular Structure, Temperature.

Abstract

1,1-Divinyl-2-phenylcyclopropanes are entry points to a rich area of rearrangement chemistry. With N,N-diallyl amide substrates, tandem radical cyclizations can be initiated at room temperature. Warming provides products of pure thermal rearrangements with acids, ester, and amides. These isomerizations give vinylcyclopentenes resulting from divinylcyclopropane rearrangements and more deeply rearranged tricyclic spirolactams resulting from aromatic Cope rearrangements followed by ene reactions. Conversion of the carbonyl group to an alcohol or ether opens retro-ene pathways followed by either tautomerization or Claisen rearrangement.

DOI: 10.1021/ja510608u
PubMed: 25530073

Links to Exploration step

pubmed:25530073

Le document en format XML

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<author><name sortKey="Hay, E Ben" sort="Hay, E Ben" uniqKey="Hay E" first="E Ben" last="Hay">E Ben Hay</name>
<affiliation><nlm:affiliation>Department of Chemistry, University of Pittsburgh , Pittsburgh, Pennsylvania 15260, United States.</nlm:affiliation>
</affiliation>
</author>
<author><name sortKey="Zhang, Hanmo" sort="Zhang, Hanmo" uniqKey="Zhang H" first="Hanmo" last="Zhang">Hanmo Zhang</name>
</author>
<author><name sortKey="Curran, Dennis P" sort="Curran, Dennis P" uniqKey="Curran D" first="Dennis P" last="Curran">Dennis P. Curran</name>
</author>
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<term>Esters (chemistry)</term>
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<term>Temperature</term>
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<front><div type="abstract" xml:lang="en">1,1-Divinyl-2-phenylcyclopropanes are entry points to a rich area of rearrangement chemistry. With N,N-diallyl amide substrates, tandem radical cyclizations can be initiated at room temperature. Warming provides products of pure thermal rearrangements with acids, ester, and amides. These isomerizations give vinylcyclopentenes resulting from divinylcyclopropane rearrangements and more deeply rearranged tricyclic spirolactams resulting from aromatic Cope rearrangements followed by ene reactions. Conversion of the carbonyl group to an alcohol or ether opens retro-ene pathways followed by either tautomerization or Claisen rearrangement.</div>
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<CommentsCorrectionsList><CommentsCorrections RefType="Cites"><RefSource>Org Lett. 2012 Feb 3;14(3):934-7</RefSource>
<PMID Version="1">22242696</PMID>
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<CommentsCorrections RefType="Cites"><RefSource>J Am Chem Soc. 2012 Oct 3;134(39):16139-42</RefSource>
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<CommentsCorrections RefType="Cites"><RefSource>Chem Rev. 2007 Jul;107(7):3117-79</RefSource>
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<CommentsCorrections RefType="Cites"><RefSource>J Am Chem Soc. 2007 Jan 24;129(3):562-8</RefSource>
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<CommentsCorrections RefType="Cites"><RefSource>Chemistry. 2009;15(14):3509-25</RefSource>
<PMID Version="1">19219879</PMID>
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<CommentsCorrections RefType="Cites"><RefSource>Org Lett. 2011 Oct 21;13(20):5468-71</RefSource>
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<CommentsCorrections RefType="Cites"><RefSource>Org Lett. 2011 Aug 19;13(16):4474-6</RefSource>
<PMID Version="1">21786746</PMID>
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<CommentsCorrections RefType="Cites"><RefSource>Nat Chem. 2014 Jan;6(1):34-40</RefSource>
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<CommentsCorrections RefType="Cites"><RefSource>J Org Chem. 2001 Dec 28;66(26):8751-9</RefSource>
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<CommentsCorrections RefType="Cites"><RefSource>J Am Chem Soc. 2011 Jul 13;133(27):10376-8</RefSource>
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<CommentsCorrections RefType="Cites"><RefSource>Angew Chem Int Ed Engl. 2010 Jul 5;49(29):4864-76</RefSource>
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<CommentsCorrections RefType="Cites"><RefSource>Org Lett. 2011 Apr 1;13(7):1778-80</RefSource>
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<CommentsCorrections RefType="Cites"><RefSource>Chem Rev. 2003 Apr;103(4):1197-212</RefSource>
<PMID Version="1">12683781</PMID>
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<CommentsCorrections RefType="Cites"><RefSource>Org Lett. 2014 Jan 3;16(1):94-7</RefSource>
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Rearrangement reactions of 1,1-divinyl-2-phenylcyclopropanes.

Rearrangement reactions of 1,1-divinyl-2-phenylcyclopropanes.

Source :

English descriptors

Abstract

Links to Exploration step

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri

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