Synlett 1999; 1999(S1): 921-924
DOI: 10.1055/s-1999-3118
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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 Schröder
  • *School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK; Fax +44(1 15)9 51 35 63; E-mail: m.schroder@nottingham.ac.uk
Further Information

Publication History

Publication Date:
31 December 1999 (online)

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.