A high-yield, one-step synthesis of o-phenylene ethynylene cyclic trimer via precipitation-driven alkyne metathesis

Wei Zhang; Scott M. Brombosz; Jose L. Mendoza; Jeffrey S. Moore

doi:10.1021/jo0517803

A high-yield, one-step synthesis of o-phenylene ethynylene cyclic trimer via precipitation-driven alkyne metathesis

Wei Zhang, Scott M. Brombosz, Jose L. Mendoza, Jeffrey S. Moore

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

Abstract

A shape-persistent, conjugated o-phenylene ethynylene cyclic trimer was prepared in one step from tetrasubstituted benzene monomer 4 in 86% isolated yield through precipitation-driven alkyne metathesis. The template-free, selective generation of the molecular triangle 5 is a thermodynamically favored process and under equilibrium control. A novel tetrameric macrocycle 7 was generated via scrambling metathesis between tricycle 5 and hexacycle 6 using this dynamic covalent chemistry.

Original language	English (US)
Pages (from-to)	10198-10201
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	70
Issue number	24
DOIs	https://doi.org/10.1021/jo0517803
State	Published - Nov 25 2005

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Organic Chemistry

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10.1021/jo0517803

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abstract = "A shape-persistent, conjugated o-phenylene ethynylene cyclic trimer was prepared in one step from tetrasubstituted benzene monomer 4 in 86% isolated yield through precipitation-driven alkyne metathesis. The template-free, selective generation of the molecular triangle 5 is a thermodynamically favored process and under equilibrium control. A novel tetrameric macrocycle 7 was generated via scrambling metathesis between tricycle 5 and hexacycle 6 using this dynamic covalent chemistry.",

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AU - Moore, Jeffrey S.

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AB - A shape-persistent, conjugated o-phenylene ethynylene cyclic trimer was prepared in one step from tetrasubstituted benzene monomer 4 in 86% isolated yield through precipitation-driven alkyne metathesis. The template-free, selective generation of the molecular triangle 5 is a thermodynamically favored process and under equilibrium control. A novel tetrameric macrocycle 7 was generated via scrambling metathesis between tricycle 5 and hexacycle 6 using this dynamic covalent chemistry.

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A high-yield, one-step synthesis of o-phenylene ethynylene cyclic trimer via precipitation-driven alkyne metathesis

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