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Related Experiment Videos

(1E,3E,5E)-1,2,3,4,5,6-Hexafluoro-1,6-diphenylhexatriene

Swenson1, Gao, Burton

  • 1Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA. dale-swenson@uiowa.edu.

Acta Crystallographica. Section C, Crystal Structure Communications
|August 16, 2000
PubMed
Summary

A novel fluorinated triene was synthesized using palladium-catalyzed coupling. Its crystal structure revealed a specific isomer with non-coplanar double bonds due to fluorine steric hindrance.

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Ferromagnetic Ordering in a Two-Dimensional Copper Complex with Dual End-to-End and End-On Azide Bridges This work was supported by the National Natural Science Foundation of China (NSF 29631040 and 29929001), The Major State Basic Research Development Program (Grant No. G2000077500 and No. G1998061306), and the Malaysian Government research grant R&D No. 305/pfizik/622004.

Angewandte Chemie (International ed. in English)·2000

Area of Science:

  • Organic Chemistry
  • Materials Science

Background:

  • Fluorinated organic compounds exhibit unique electronic and steric properties.
  • Trienes are versatile building blocks in organic synthesis.
  • Palladium-catalyzed cross-coupling reactions are crucial for C-C bond formation.

Purpose of the Study:

  • To synthesize a novel fluorinated triene (C18H10F6).
  • To determine the stereochemistry and solid-state structure of the synthesized triene.
  • To investigate the impact of fluorine substituents on the triene's geometry.

Main Methods:

  • Synthesis via Pd(0) coupling reaction.
  • Utilized (E)-(1,2-difluoro-1,2-ethenediyl)bis(tributylstannane) and (Z)-beta-iodo-alpha,beta-difluorostyrene.
  • Characterization using X-ray crystallography.

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Main Results:

  • Successfully synthesized the title triene, C18H10F6.
  • The crystal structure confirmed the 1E,3E,5E isomer.
  • Steric interactions of fluorine atoms caused non-planar double bonds, with terminal double bond planes nearly perpendicular.

Conclusions:

  • The Pd(0) coupling is effective for synthesizing complex fluorinated trienes.
  • Fluorine substitution significantly influences molecular geometry and conformation.
  • The study provides insights into the structure-property relationships of fluorinated organic molecules.