Flash vacuum pyrolysis of stabilised phosphorus ylides .7. Cyclisation of amino acid derived alpha-phthalimidoacyl ylides to give pyrroloisoindolediones

R Alan Aitken, H R Cooper, A P Mehrotra

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24 Citations (Scopus)

Abstract

A series of 11 amino acid-derived stabilised ylides 12-14 and 16 have been prepared and characterised. In one case, for compound 17, an X-ray structure determination supports formulation of the compounds as phosphonium enolates. Flash vacuum pyrolysis (FVP) of 12 and 13 at 500 degrees C results ih loss of R(3)(2)PO between the ylide function and one carbonyl of the phthalimido group to give products characterised spectroscopically as the pyrroloisoindolediones 18. The identity of these is also supported by the results of C-13 and N-15 labelling experiments, but owing to their high reactivity complete separation from the phosphine oxide was not generally possible even when Bu(3)PO rather than Ph(3)PO was involved. Chromatographic purification of 29, similarly produced by FVP of 14, led to partial hydrolysis, rearrangement and decarboxylation to give 30. FVP of 12 at 750 degrees C gave the 1-unsubstituted pyrroloisoindolediones 19 in two cases.

Original languageEnglish
Pages (from-to)475-483
Number of pages9
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number5
DOIs
Publication statusPublished - 7 Mar 1996

Keywords

  • CARBOXYLIC-ACIDS
  • MECHANISM
  • GABA

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