Syntheses, structure, and reactivity of acyclic enetriyne and enetetrayne derivatives

John D Spence; Miranda L Lackie; Nicola A Clayton; Sergio A Toscano; Michelle A Farmer; Esfir Popova; Marilyn M Olmstead

doi:10.1016/j.tetlet.2014.01.076

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Syntheses, structure, and reactivity of acyclic enetriyne and enetetrayne derivatives

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Syntheses, structure, and reactivity of acyclic enetriyne and enetetrayne derivatives

John D Spence, Miranda L Lackie, Nicola A Clayton, Sergio A Toscano, Michelle A Farmer, Esfir Popova and Marilyn M Olmstead

Tetrahedron letters, Vol.55(9), pp.1569-1572

02/26/2014

DOI: https://doi.org/10.1016/j.tetlet.2014.01.076

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https://hdl.handle.net/20.500.12741/rep:5005

Abstract

Bergman cyclization

Enetriyne

Enetetrayne

Buta-1,3-diynylbenzene

Sonogashira coupling of buta-1,3-diynylbenzene with ((2-iodophenyl)ethynyl)trimethylsilane and 1,2-diiodobenzene led to the novel enetriyne, 1-ethynyl-2-(phenylbuta-1,3-diynyl)benzene, and enetetrayne, 1,2-bis(phenylbuta-1,3-diynyl)benzene, respectively. Solid state structural and thermal analyses are also described. In solution, 1-ethynyl-2-(phenylbuta-1,3-diynyl)benzene was found to undergo thermal Bergman cyclization to afford 2-(phenylethynyl)naphthalene.

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Title: Syntheses, structure, and reactivity of acyclic enetriyne and enetetrayne derivatives
Creators: John D Spence - Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819, United States
Miranda L Lackie - Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819, United States
Nicola A Clayton - Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819, United States
Sergio A Toscano - Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819, United States
Michelle A Farmer - Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819, United States
Esfir Popova - Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819, United States
Marilyn M Olmstead - Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616, United States
Academic Unit: Chemistry Department
Publisher: Elsevier Ltd
Publication Details: 02/26/2014
Identifiers: 99257847424001671; https://hdl.handle.net/20.500.12741/rep:5005; https://doi.org/10.1016/j.tetlet.2014.01.076
Language: English

Syntheses, structure, and reactivity of acyclic enetriyne and enetetrayne derivatives

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