Novel spiro cyclisations of N-acyliminium ions involving an aromatic π-nucleophile

Patrick D. Bailey; Keith M. Morgan; David I. Smith; John M. Vernon

doi:10.1016/0040-4039(94)88240-1

Novel spiro cyclisations of N-acyliminium ions involving an aromatic π-nucleophile

Patrick D. Bailey, Keith M. Morgan, David I. Smith, John M. Vernon

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article

Abstract

Several spiro 2-pyrrolidin-5-ones were obtained by a two-step procedure from N-substituted succinimides, involving spiro cyclisation of N-acyliminium ion intermediates in refluxing trifluoroacetic acid; in all cases cyclisation utilised a tethered aromatic p-nucleophile, and ring-closure followed 5- or 6-exo-trig pathways.

Original language	English
Pages (from-to)	7115-7118
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	38
DOIs	https://doi.org/10.1016/0040-4039(94)88240-1
Publication status	Published - 1994

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Bailey, P. D., Morgan, K. M., Smith, D. I., & Vernon, J. M. (1994). Novel spiro cyclisations of N-acyliminium ions involving an aromatic π-nucleophile. Tetrahedron Letters, 35(38), 7115-7118. https://doi.org/10.1016/0040-4039(94)88240-1

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abstract = "Several spiro 2-pyrrolidin-5-ones were obtained by a two-step procedure from N-substituted succinimides, involving spiro cyclisation of N-acyliminium ion intermediates in refluxing trifluoroacetic acid; in all cases cyclisation utilised a tethered aromatic p-nucleophile, and ring-closure followed 5- or 6-exo-trig pathways.",

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AU - Smith, David I.

AU - Vernon, John M.

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AB - Several spiro 2-pyrrolidin-5-ones were obtained by a two-step procedure from N-substituted succinimides, involving spiro cyclisation of N-acyliminium ion intermediates in refluxing trifluoroacetic acid; in all cases cyclisation utilised a tethered aromatic p-nucleophile, and ring-closure followed 5- or 6-exo-trig pathways.

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