The Bergman reaction as a synthetic tool: Advantages and restrictions

Daniel M. Bowles; Grant J. Palmer; Chad A. Landis; John L. Scott; John E. Anthony

doi:10.1016/S0040-4020(01)00247-2

The Bergman reaction as a synthetic tool: Advantages and restrictions

Daniel M. Bowles, Grant J. Palmer, Chad A. Landis, John L. Scott, John E. Anthony

Research output: Contribution to journal › Article › peer-review

62 Scopus citations

Abstract

The Bergman cycloaromatization reaction efficiently converts easily prepared acyclic enediynes into aromatic rings. In order to prepare larger, functionalized fused aromatic systems using this reaction, a thorough understanding of how functionalization affects cycloaromatization is necessary. We present here our studies on the influence of substituents at three different functionalization sites on cycloaromatization, and how these functional groups can be tailored to prepare more complex systems.

Original language	English
Pages (from-to)	3753-3760
Number of pages	8
Journal	Tetrahedron
Volume	57
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4020(01)00247-2
State	Published - Apr 23 2001

Bibliographical note

Funding Information:
This work was supported by the National Science Foundation (CAREER Award CHE 9875123), the Office of Naval Research and the University of Kentucky Research Foundation. NMR Facilities used in this research were enhanced by funds from the CRIF program of the National Science Foundation (CHE 997841) and from the Research Challenge Trust Fund of the University of Kentucky.

Funding

This work was supported by the National Science Foundation (CAREER Award CHE 9875123), the Office of Naval Research and the University of Kentucky Research Foundation. NMR Facilities used in this research were enhanced by funds from the CRIF program of the National Science Foundation (CHE 997841) and from the Research Challenge Trust Fund of the University of Kentucky.

Funders	Funder number
National Science Foundation (NSF)	CHE 9875123
Office of Naval Research
University of Kentucky
Northern Kentucky University Research Foundation	CHE 997841

Keywords

Acenes
Bergman reaction
Cycloaromatization
Functionalization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(01)00247-2

Cite this

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abstract = "The Bergman cycloaromatization reaction efficiently converts easily prepared acyclic enediynes into aromatic rings. In order to prepare larger, functionalized fused aromatic systems using this reaction, a thorough understanding of how functionalization affects cycloaromatization is necessary. We present here our studies on the influence of substituents at three different functionalization sites on cycloaromatization, and how these functional groups can be tailored to prepare more complex systems.",

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note = "Funding Information: This work was supported by the National Science Foundation (CAREER Award CHE 9875123), the Office of Naval Research and the University of Kentucky Research Foundation. NMR Facilities used in this research were enhanced by funds from the CRIF program of the National Science Foundation (CHE 997841) and from the Research Challenge Trust Fund of the University of Kentucky.",

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AU - Palmer, Grant J.

AU - Landis, Chad A.

AU - Scott, John L.

AU - Anthony, John E.

N1 - Funding Information: This work was supported by the National Science Foundation (CAREER Award CHE 9875123), the Office of Naval Research and the University of Kentucky Research Foundation. NMR Facilities used in this research were enhanced by funds from the CRIF program of the National Science Foundation (CHE 997841) and from the Research Challenge Trust Fund of the University of Kentucky.

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N2 - The Bergman cycloaromatization reaction efficiently converts easily prepared acyclic enediynes into aromatic rings. In order to prepare larger, functionalized fused aromatic systems using this reaction, a thorough understanding of how functionalization affects cycloaromatization is necessary. We present here our studies on the influence of substituents at three different functionalization sites on cycloaromatization, and how these functional groups can be tailored to prepare more complex systems.

AB - The Bergman cycloaromatization reaction efficiently converts easily prepared acyclic enediynes into aromatic rings. In order to prepare larger, functionalized fused aromatic systems using this reaction, a thorough understanding of how functionalization affects cycloaromatization is necessary. We present here our studies on the influence of substituents at three different functionalization sites on cycloaromatization, and how these functional groups can be tailored to prepare more complex systems.

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The Bergman reaction as a synthetic tool: Advantages and restrictions

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

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