A reiterative approach to 2,3-disubstituted naphthalenes and anthracenes

Daniel M. Bowles; John E. Anthony

doi:10.1021/ol991254w

A reiterative approach to 2,3-disubstituted naphthalenes and anthracenes

Daniel M. Bowles, John E. Anthony

Chemistry

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

74 Scopus citations

Abstract

(formula presented) Simple bis(bromoethynyl)arenediynes are easily prepared by the desilylative halogenation of the corresponding trimethylsilyl derivatives. Cycloaromatization of these halogenated enediynes leads to the otherwise difficult to prepare 2,3-dibromoarenes in good yield. Alkynylation of the resulting haloaromatic compound regenerates the soluble enediyne system, homologated by one aromatic ring. This iterative methodology can be terminated by the cycloaromatization of the unsubstituted enediyne, providing the simple acene hydrocarbon.

Original language	English
Pages (from-to)	85-87
Number of pages	3
Journal	Organic Letters
Volume	2
Issue number	1
DOIs	https://doi.org/10.1021/ol991254w
State	Published - Jan 2000

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "A reiterative approach to 2,3-disubstituted naphthalenes and anthracenes",

abstract = "(formula presented) Simple bis(bromoethynyl)arenediynes are easily prepared by the desilylative halogenation of the corresponding trimethylsilyl derivatives. Cycloaromatization of these halogenated enediynes leads to the otherwise difficult to prepare 2,3-dibromoarenes in good yield. Alkynylation of the resulting haloaromatic compound regenerates the soluble enediyne system, homologated by one aromatic ring. This iterative methodology can be terminated by the cycloaromatization of the unsubstituted enediyne, providing the simple acene hydrocarbon.",

author = "Bowles, {Daniel M.} and Anthony, {John E.}",

year = "2000",

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doi = "10.1021/ol991254w",

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AU - Anthony, John E.

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N2 - (formula presented) Simple bis(bromoethynyl)arenediynes are easily prepared by the desilylative halogenation of the corresponding trimethylsilyl derivatives. Cycloaromatization of these halogenated enediynes leads to the otherwise difficult to prepare 2,3-dibromoarenes in good yield. Alkynylation of the resulting haloaromatic compound regenerates the soluble enediyne system, homologated by one aromatic ring. This iterative methodology can be terminated by the cycloaromatization of the unsubstituted enediyne, providing the simple acene hydrocarbon.

AB - (formula presented) Simple bis(bromoethynyl)arenediynes are easily prepared by the desilylative halogenation of the corresponding trimethylsilyl derivatives. Cycloaromatization of these halogenated enediynes leads to the otherwise difficult to prepare 2,3-dibromoarenes in good yield. Alkynylation of the resulting haloaromatic compound regenerates the soluble enediyne system, homologated by one aromatic ring. This iterative methodology can be terminated by the cycloaromatization of the unsubstituted enediyne, providing the simple acene hydrocarbon.

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A reiterative approach to 2,3-disubstituted naphthalenes and anthracenes

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