Cyclodextrin-mediated regioselective photo-Fries reaction of 1-naphthyl phenyl acylates

Smriti Koodanjeri, Ajit R. Pradhan, Lakshmi S. Kaanumalle, V. Ramamurthy

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

1-Naphthyl phenyl acylates upon irradiation in solution yield eight products via β-cleavage process. However, excitation of these molecules as included in γ-cyclodextrin results in a single product (>95%). This medium dependent product selectivity is attributed to conformational and translational restrictions enforced on the reactant as well as intermediates by the cyclodextrin cavity.

Original languageEnglish (US)
Pages (from-to)3207-3210
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number15
DOIs
StatePublished - Apr 7 2003
Externally publishedYes

Keywords

  • 1-naphthyl phenyl acylates
  • Cyclodextrin
  • Photo-Fries reaction
  • Product control

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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