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A cyclodextrin-based molecular reactor to template the formation of indigoid dyes

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
44
Issue
31
Identifiers
DOI: 10.1016/s0040-4039(03)01403-5
Keywords
  • Molecular Reactors
  • Templates
  • Inclusion Complexes
  • Cyclodextrins
  • Dyes

Abstract

Abstract N, N′-Bis(6 A-deoxy-β-cyclodextrin-6 A-yl)urea behaves as a molecular reactor to bias competing reactions of indoxyl anion and isatin-5-sulfonate in water, to give indigo and indirubin-5′-sulfonate. It appears that the cyclodextrin dimer increases the relative reactivity of the isatin-5-sulfonate, by selectively complexing the reactive form. The molecular host also aligns the isatinsulfonate with indoxyl anion to favour production of indirubin-5′-sulfonate, with the result that the ratio of indigo and indirubin-5′-sulfonate produced is altered by a factor of at least 3500, without a substantial loss of yield.

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