PittsburghV1, Pmc, Curation, bibRecord, 000332

Rearrangement Reactions of 1,1-Divinyl-2-phenylcyclopropanes

Identifieur interne : 000332 ( Pmc/Curation ); précédent : 000331; suivant : 000333

Rearrangement Reactions of 1,1-Divinyl-2-phenylcyclopropanes

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

Source :

Journal of the American Chemical Society [ 0002-7863 ] ; 2014.

RBID : PMC:4304479

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.

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4304479

DOI: 10.1021/ja510608u
PubMed: 25530073
PubMed Central: 4304479

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Reactions of 1,1-Divinyl-2-phenylcyclopropanes</title>
<author><name sortKey="Hay, E Ben" sort="Hay, E Ben" uniqKey="Hay E" first="E. Ben" last="Hay">E. Ben Hay</name>
</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>
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Reactions of 1,1-Divinyl-2-phenylcyclopropanes</title>
<author><name sortKey="Hay, E Ben" sort="Hay, E Ben" uniqKey="Hay E" first="E. Ben" last="Hay">E. Ben Hay</name>
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<p>1,1-Divinyl-2-phenylcyclopropanes
are entry points to a rich area
of rearrangement chemistry. With <italic>N,N</italic>-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.</p>
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  <front><journal-meta><journal-id journal-id-type="nlm-ta">J Am Chem Soc</journal-id>
<journal-id journal-id-type="iso-abbrev">J. Am. Chem. Soc</journal-id>
<journal-id journal-id-type="publisher-id">ja</journal-id>
<journal-id journal-id-type="coden">jacsat</journal-id>
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<issn pub-type="ppub">0002-7863</issn>
<issn pub-type="epub">1520-5126</issn>
<publisher><publisher-name>American Chemical
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<article-categories><subj-group><subject>Article</subject>
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</article-categories>
<title-group><article-title>Rearrangement
Reactions of 1,1-Divinyl-2-phenylcyclopropanes</article-title>
</title-group>
<contrib-group><contrib contrib-type="author" id="ath1"><name><surname>Hay</surname>
<given-names>E. Ben</given-names>
</name>
</contrib>
<contrib contrib-type="author" id="ath2"><name><surname>Zhang</surname>
<given-names>Hanmo</given-names>
</name>
</contrib>
<contrib contrib-type="author" corresp="yes" id="ath3"><name><surname>Curran</surname>
<given-names>Dennis P.</given-names>
</name>
<xref rid="cor1" ref-type="other">*</xref>
</contrib>
<aff id="aff1">Department of Chemistry,<institution>University of Pittsburgh</institution>
, Pittsburgh, Pennsylvania 15260,<country>United States</country>
</aff>
</contrib-group>
<author-notes><corresp id="cor1"><label>*</label>
E-mail: <email>curran@pitt.edu</email>
.</corresp>
</author-notes>
<pub-date pub-type="pmc-release"><day>05</day>
<month>12</month>
<year>2015</year>
</pub-date>
<pub-date pub-type="epub"><day>05</day>
<month>12</month>
<year>2014</year>
</pub-date>
<pub-date pub-type="ppub"><day>14</day>
<month>01</month>
<year>2015</year>
</pub-date>
<volume>137</volume>
<issue>1</issue>
<fpage>322</fpage>
<lpage>327</lpage>
<history><date date-type="received"><day>15</day>
<month>10</month>
<year>2014</year>
</date>
</history>
<permissions><copyright-statement>Copyright © 2014 American
Chemical Society</copyright-statement>
<copyright-year>2014</copyright-year>
<copyright-holder>American
Chemical Society</copyright-holder>
<license><license-p>This is an open access article published under an ACS AuthorChoice <ext-link ext-link-type="uri" xlink:href="http://pubs.acs.org/page/policy/authorchoice_termsofuse.html">License</ext-link>
, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.</license-p>
</license>
</permissions>
<abstract><p content-type="toc-graphic"><graphic xlink:href="ja-2014-10608u_0014" id="ab-tgr1"></graphic>
</p>
<p>1,1-Divinyl-2-phenylcyclopropanes
are entry points to a rich area
of rearrangement chemistry. With <italic>N,N</italic>-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.</p>
</abstract>
<funding-group><funding-statement><funding-source>National Institutes of Health, United States</funding-source>
</funding-statement>
</funding-group>
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</front>
</pmc>
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Rearrangement Reactions of 1,1-Divinyl-2-phenylcyclopropanes

Rearrangement Reactions of 1,1-Divinyl-2-phenylcyclopropanes

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Abstract

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