Jump to main content
Jump to site search

Issue 17, 2001
Previous Article Next Article

Highly peri- and stereoselective intramolecular photocycloaddition and cyclisation of N-(1-naphthylethyl)prop-2-enamides

Author affiliations

Abstract

Control of three modes of intramolecular reactions, [2+2] and [4+2] cycloadditions, and Type-II cyclisation, is attempted in the photochemical reaction of N-(naphthylethyl)prop-2-enamides. The reactions are affected by the enamide substituents and the sensitisation conditions used. Acryloyl derivatives undergo [2+2] cycloaddition and Type-II cyclisation. The two reactions occur selectively depending on the sensitiser used, benzophenone sensitisation affording the [2+2] cycloadducts whereas the Type-II cyclisation products are obtained exclusively by benzene sensitisation. In contrast, photolysis of cinnamoyl derivatives results in the formation of [4+2] cycloadducts.

Graphical abstract: Highly peri- and stereoselective intramolecular photocycloaddition and cyclisation of N-(1-naphthylethyl)prop-2-enamides

Back to tab navigation

Publication details

The article was received on 18 Jan 2001, accepted on 03 Jul 2001 and first published on 09 Aug 2001


Article type: Paper
DOI: 10.1039/B100678I
Citation: J. Chem. Soc., Perkin Trans. 1, 2001,0, 2082-2088
  •   Request permissions

    Highly peri- and stereoselective intramolecular photocycloaddition and cyclisation of N-(1-naphthylethyl)prop-2-enamides

    S. Kohmoto, Y. Miyaji, M. Tsuruoka, K. Kishikawa, M. Yamamoto and K. Yamada, J. Chem. Soc., Perkin Trans. 1, 2001, 0, 2082
    DOI: 10.1039/B100678I

Search articles by author

Spotlight

Advertisements