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Organic Base-Mediated Wittig Reaction of Perfluorohalogenated Benzaldehydes for Designing Halogen Bond-Driven Smart Polymer Materials: Toward Digitalization as Reliable Strategy in Organic Synthesis

19 May 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The Wittig reaction of perfluorohalobenzaldehydes was systematically studied to investigate perfluorohalostyrenes (TFXS) as functional monomers of halogen bond-driven smart polymer materials. The reaction proceeded efficiently in THF using 1,1,3,3-tetramethylguanidine as the organic base. The number of nitrogen atoms in the organic base played an important role in the production of TFXS. The present approach does not only contribute to the study of halogen bond-based functional molecules but also presents digitalization as a potential strategy in organic synthesis.

Supplementary materials

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Supporting Information
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1. General information 2. Synthesis of 2,3,5,6-tetrafluoro-4-halobenzaldehydes 3. Synthesis and characterization of 2.3.5.6-tetrafluoro-4-halostyrenes 4. Initial study of Wittig reaction 5. DFT calculations 6. Correlation analyses 7. References 8. NMR spectra 9. Cartesian coordinates
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