Controlled photochemical reaction of 4-oxo(phenylacetyl) morpholine and 1-(phenylglyoxylyl)piperidine in solid supramolecular systems

Tali Lavy, Yana Sheynin, Hazel A. Sparkes, Judith A. K. Howard, Menahem Kaftory*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

14 Citations (Scopus)

Abstract

Six inclusion compounds containing a photoreactive guest molecule, 4-oxo( phenylacetyl) morpholine or 1-(phenylglyoxylyl) piperidine, with different host molecules have been crystallized. The guest molecules underwent photochemical reaction upon irradiation. Examining their structures suggests that gamma-hydrogen abstraction by an oxygen, the first step in cyclization of alpha-oxoamides, should be possible in all cases. In four cases crystallinity was maintained during and at the end of the conversion process i.e. the process was a single-crystal to single-crystal transformation. The crystal structure of the product crystals revealed that in two of the inclusion compounds the product obtained is a result of enclosure to a four-membered ring while in the other two the product obtained results from enclosure to a five-membered ring. The morpholine molecules adopt two different conformations. The photochemical reaction may take different courses either as a result of the different conformation or as a result of the different shapes of the cavities provided by the host molecules.

Original languageEnglish
Pages (from-to)734-739
Number of pages6
JournalCrystEngComm
Volume10
Issue number6
DOIs
Publication statusPublished - 2008

Keywords

  • TO-SINGLE-CRYSTAL
  • ASYMMETRIC INDUCTION
  • STATE PHOTOCHEMISTRY
  • INCLUSION-COMPOUNDS
  • II REACTIONS
  • PHOTOCYCLIZATION
  • HOST
  • MOLECULES
  • PHOTODIMERIZATION
  • ZEOLITES

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