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Pinacolophanes as versatile precursor for the practical synthesis of tolanophanes

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Abstract

A new strategy for the synthesis of tolanophanes was investigated. The coupling of bridged dialdehydes gave selectively the corresponding monomer of pinacolophanes in quantitative yields under a simple and clean reaction condition. Without any further purification, pinacolophanes were quantitatively converted to tolanophanes using a two-step bromination–dehydrobromination process. The overall yield of this practical protocol is upper than 90%. This precursor is highly advantageous compared to the reported stilbenophane in terms of safety, operational simplicity, easy workup, and high efficiency.

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Authors and Affiliations

  1. Nano and Organic Synthesis Laboratory, Chemistry and Chemical Engineering Research Center of Iran, Pajoohesh Blvd., 17th Km of Tehran-Karaj Highway, Tehran, 14968-13151, Iran

    Hossein Reza Darabi, Saeed Rastgar, Kioumars Aghapoor & Farshid Mohsenzadeh

Authors
  1. Hossein Reza Darabi
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  2. Saeed Rastgar
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  3. Kioumars Aghapoor
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  4. Farshid Mohsenzadeh
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Correspondence to Hossein Reza Darabi.

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Darabi, H.R., Rastgar, S., Aghapoor, K. et al. Pinacolophanes as versatile precursor for the practical synthesis of tolanophanes. Monatsh Chem 149, 1121–1124 (2018). https://doi.org/10.1007/s00706-017-2125-3

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  • DOI: https://doi.org/10.1007/s00706-017-2125-3

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