Synthesis of a protonated C-2-symmetric N,N-chiral "proton sponge"

JPH Charmant, GC Lloyd-Jones*, TM Peakman, RL Woodward

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The hydrogen iodide salt of 1,8-bis-(N-benzyl-N-methylamino)naphthalene was synthesised as an 89/11 ratio of diastereomers in good yield. The structure of the major (+)-(RNRN/SNSN) diastereomer was determined by single crystal X-ray diffraction. The minor diastereomer is shown to be the meso-(RNSN) form by performing H-1 NMR n.O.e studies on isotopically desymmetrized 1-(N-benzyl-N-[C-13]-methylamino)-8-(N'-benzyl-N'-methylamino) naphthalene (HI salt). The half-life of interconversion of meso and dl forms is less than 2 minutes in CD2Cl2, at ambient temperature. (C) 1998 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)4733-4736
Number of pages4
JournalTetrahedron Letters
Volume39
Issue number26
Publication statusPublished - 25 Jun 1998

Keywords

  • HYDROGEN-BONDS
  • BASICITIES
  • CATALYSIS

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