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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title = "Novel spiro cyclisations of N-acyliminium ions involving an aromatic π-nucleophile",

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.",

author = "Bailey, {Patrick D.} and Morgan, {Keith M.} and Smith, {David I.} and Vernon, {John M.}",

year = "1994",

doi = "10.1016/0040-4039(94)88240-1",

language = "English",

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journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "38",

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T1 - Novel spiro cyclisations of N-acyliminium ions involving an aromatic π-nucleophile

AU - Bailey, Patrick D.

AU - Morgan, Keith M.

AU - Smith, David I.

AU - Vernon, John M.

PY - 1994

Y1 - 1994

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=0027940177&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(94)88240-1

DO - 10.1016/0040-4039(94)88240-1

M3 - Article

VL - 35

SP - 7115

EP - 7118

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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ER -