Syntheses,structure, and reactivity of acyclic enetriyne and enetetrayne derivatives |
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Authors: | John D. Spence Miranda L. Lackie Nicola A. Clayton Sergio A. Toscano Michelle A. Farmer Esfir Popova Marilyn M. Olmstead |
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Affiliation: | 1. Department of Chemistry, California State University, Sacramento, 6000 J Street, Sacramento, CA 95819, United States;2. Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616, United States |
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Abstract: | 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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Keywords: | Buta-1,3-diynylbenzene Enetriyne Enetetrayne Bergman cyclization |
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