PittsburghV1, Main, Exploration, bibRecord, 001760

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

Identifieur interne : 001760 ( Main/Exploration ); précédent : 001759; suivant : 001761

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

Descripteurs français

KwdFr :
- Acides (), Amides (), Composés vinyliques (), Cyclisation, Cyclopropanes (), Esters (), Radicaux libres (), Radicaux libres (synthèse chimique), Structure moléculaire, Température.
MESH :
- synthèse chimique : Radicaux libres.
- Acides, Amides, Composés vinyliques, Cyclisation, Cyclopropanes, Esters, Radicaux libres, Structure moléculaire, Température.

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.

Url:

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

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

Affiliations:

Le document en format XML

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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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<author><name sortKey="Zhang, Hanmo" sort="Zhang, Hanmo" uniqKey="Zhang H" first="Hanmo" last="Zhang">Hanmo Zhang</name>
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<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>
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<term>Esters (chemistry)</term>
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<term>Cyclopropanes ()</term>
<term>Esters ()</term>
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<term>Radicaux libres (synthèse chimique)</term>
<term>Structure moléculaire</term>
<term>Température</term>
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<term>Cyclopropanes</term>
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<term>Free Radicals</term>
<term>Vinyl Compounds</term>
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<front><div type="abstract" xml:lang="en"><p content-type="toc-graphic"><graphic xlink:href="ja-2014-10608u_0014" id="ab-tgr1"></graphic>
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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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Rearrangement Reactions of 1,1-Divinyl-2-phenylcyclopropanes

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

Source :

Descripteurs français

English descriptors

Abstract

Links toward previous steps (curation, corpus...)

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