• Title/Summary/Keyword: Tetrahydropyranyl ethers

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An Efficient Method for Selective Deprotection of Trimethylsilyl Ethers and Tetrahydropyranyl Ethers under Solvent-free Conditions

  • Hajipour, A.R.;Bagheri, Hamid R.;Ruoho, Arnold E.
    • Bulletin of the Korean Chemical Society
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    • v.26 no.11
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    • pp.1689-1691
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    • 2005
  • 1-Butyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate (BAABOD) 3 is a useful reagent for the selective cleavage of trimethylsilyl ethers and tetrahydropyranyl ethers to their corresponding aldehydes and ketones in the presence of $AlCl_3$ under solvent-free conditions. This method is very simple and efficient and the reaction has been carried out under solvent-free conditions in the presence of a catalytically amount of aluminum chloride.

Acetyl Chloride-mediated Mild and Chemoselective Attachment and Removal of Tetrahydropyranyl (THP) Group

  • Yeom, Chang-Eun;Shin, Yong-Je;Kim, B.-Moon
    • Bulletin of the Korean Chemical Society
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    • v.28 no.1
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    • pp.103-107
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    • 2007
  • A mild, chemoselective and convenient method for the formation and deprotection of tetrahydropyranyl ethers is described. With 1-5 mol% of acetyl chloride and slightly excess dihydropyran in methylene chloride or in neat dihydropyran, the formation of THP ethers from the corresponding alcohols was accomplished in the presence of many acid-sensitive functional groups. Efficient cleavage of THP ethers was also accomplished with the same reagent by switching the solvent to methanol.

New Crown Compounds Derived from 1,2-Bis(2-hydroxybenzyl)benzene (II) : Bisaryl Crowns

  • Lee, Woo-Young;Jung, Jae-Do;Park, Chang-Hee;Sim, Won-Bo;Park, Oee-Sook
    • Bulletin of the Korean Chemical Society
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    • v.11 no.4
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    • pp.350-354
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    • 1990
  • New bisaryl corands (crown ethers) bearing 1,2-dibenzyl- and 1,2-dibenzoylbenzene subunits have been synthesized: The reaction of 1,2-bis(2-hydroxybenzyl)benzene in base with mono-tetrahydropyranyl oligoethylene glycol tosylate, deprotection of the bis-condensation product to give a corresponding diol, tosylation of the free hydroxyls of the diol, and condensation of the ditosylate in base with 1,2-bis(2-hydroxybenzyl)benzene afforded a new type of bisaryl corand(Ⅰ) of 1,2-dibenzyl-benazene system. Oxidation of the benzylic positions of the corands (Ⅰ) furnished novel aromatic corands(Ⅱ) containing partly carbonyl functions.