Synthesis of Terminal 1,3‐Diynes via Sonogashira Coupling of Vinylidene Chloride Followed by Elimination. Preparation of 1,3‐Decadiyne

The [n]dendralenes are a family of acyclic hydrocarbons which, by virtue of their ability to rapidly generate structural complexity, have attracted significant recent synthetic attention. [3]Dendralene through [8]dendralene have been previously prepared but no higher member of the family has been reported to date. Here, we describe the first chemical syntheses of the "higher" dendralenes, [9]dendralene through [12]dendralene. We also report a detailed investigation into the spectroscopic properties and chemical reactivity of the complete family of fundamental hydrocarbons, [3]dendralene to [12]dendralene. These studies reveal the first case of diminishing alternation in behavior in a series of related structures. We also report a comprehensive series of computational studies, which trace this dampening oscillatory effect in both spectroscopic measurements and chemical reactivity to conformational preferences.

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Synthesis of Terminal 1,3‐Diynes via Sonogashira Coupling of Vinylidene Chloride Followed by Elimination. Preparation of 1,3‐Decadiyne

Abstract: n ‐Butylamine 1‐Octyne Vinylidene chloride 2‐Chloro‐1‐decen‐3‐yne Copper (I) iodide 1, 3‐Decadiyne Diisopropylamine

Cited by 3 publications

References 23 publications

Organopalladium Chemistry

Organopalladium Chemistry

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Discovery and Computational Rationalization of Diminishing Alternation in [n]Dendralenes

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