Stereochemistry and ring opening of a carbocyclic analogue of a 1-oxapenam

Demetrios Agathocleous; Graham Cox; Michael I. Page

doi:10.1016/S0040-4039(00)84333-6

Stereochemistry and ring opening of a carbocyclic analogue of a 1-oxapenam

Demetrios Agathocleous, Graham Cox, Michael I. Page

School of Applied Sciences

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

The cycloaddition of succinimido ketene to 2,3-dihydrofuran yields P-exo-succinimido bicyclo [3.2.0] 2-oxoheptan-6-one. This unusual stereochemistry is confirmed by ¹H NMR and X-ray crystallography. The cyclobutanone product undergoes ring opening in concentrated hydrochloric acid to give 1-succinimido-5-chloro-2-pentanone.

Original language	English
Pages (from-to)	1631-1634
Number of pages	4
Journal	Tetrahedron Letters
Volume	27
Issue number	14
DOIs	https://doi.org/10.1016/S0040-4039(00)84333-6
Publication status	Published - 1986

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title = "Stereochemistry and ring opening of a carbocyclic analogue of a 1-oxapenam",

abstract = "The cycloaddition of succinimido ketene to 2,3-dihydrofuran yields P-exo-succinimido bicyclo [3.2.0] 2-oxoheptan-6-one. This unusual stereochemistry is confirmed by 1H NMR and X-ray crystallography. The cyclobutanone product undergoes ring opening in concentrated hydrochloric acid to give 1-succinimido-5-chloro-2-pentanone.",

author = "Demetrios Agathocleous and Graham Cox and Page, {Michael I.}",

year = "1986",

doi = "10.1016/S0040-4039(00)84333-6",

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journal = "Tetrahedron Letters",

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T1 - Stereochemistry and ring opening of a carbocyclic analogue of a 1-oxapenam

AU - Agathocleous, Demetrios

AU - Cox, Graham

AU - Page, Michael I.

PY - 1986

Y1 - 1986

N2 - The cycloaddition of succinimido ketene to 2,3-dihydrofuran yields P-exo-succinimido bicyclo [3.2.0] 2-oxoheptan-6-one. This unusual stereochemistry is confirmed by 1H NMR and X-ray crystallography. The cyclobutanone product undergoes ring opening in concentrated hydrochloric acid to give 1-succinimido-5-chloro-2-pentanone.

AB - The cycloaddition of succinimido ketene to 2,3-dihydrofuran yields P-exo-succinimido bicyclo [3.2.0] 2-oxoheptan-6-one. This unusual stereochemistry is confirmed by 1H NMR and X-ray crystallography. The cyclobutanone product undergoes ring opening in concentrated hydrochloric acid to give 1-succinimido-5-chloro-2-pentanone.

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U2 - 10.1016/S0040-4039(00)84333-6

DO - 10.1016/S0040-4039(00)84333-6

M3 - Article

AN - SCOPUS:0022626188

VL - 27

SP - 1631

EP - 1634

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 14

ER -

Stereochemistry and ring opening of a carbocyclic analogue of a 1-oxapenam

Abstract

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