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Syntheses,structure, and reactivity of acyclic enetriyne and enetetrayne derivatives
Authors:John D. Spence  Miranda L. Lackie  Nicola A. Clayton  Sergio A. Toscano  Michelle A. Farmer  Esfir Popova  Marilyn M. Olmstead
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
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.
Keywords:Buta-1,3-diynylbenzene   Enetriyne   Enetetrayne   Bergman cyclization
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