6-Amino[14]aneS4: A new amine-functionalised crown chalcogenide

Liam R Sutton, Alexander J Blake, Paul A Cooke, Robert O Gould, Simon Parsons, Martin Schroder

    Research output: Contribution to journalArticlepeer-review

    Abstract

    We report the first synthesis of 6-amino-1,4,8,11-tetrathiacyclotetradecane (6-amino[14]aneS4, 1) which is, to our knowledge, the first example of a crown chalcogenide incorporating a primary amine on the carbon backbone. Both routes discussed herein have as their key step functional group conversion from hydroxyl to phthalimide-protected amine using the Mitsunobu reaction. The first route entails Mitsunobu reaction of 6-hydroxy[14]aneS4 (2) with phthalimide and results in the formation of a mixture of products whose distribution implies the common intermediacy of an episulfonium ion (EPSI). In the second pathway, 1,3-dichloro-2-propanol is converted 2-amino-1,3-dichloropropane N-phthalimide (3) from which 6-amino[14]aneS4 N-phthalimide (4) can be obtained by cyclisation with 1, 4, 8, 11 N-tetrathiaundecane under high dilution conditions in DMF in the presence of Cs2CO3. Deprotection of 4 with NH2NH2 hydrate yields the target molecule, 1.
    Original languageEnglish
    Pages (from-to)921-924
    Number of pages4
    JournalSYNLETT
    Issue numberSupplt. 1
    DOIs
    Publication statusPublished - 1999

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