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

Demetrios Agathocleous, Graham Cox, Michael I. Page

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)1631-1634
Number of pages4
JournalTetrahedron Letters
Volume27
Issue number14
DOIs
Publication statusPublished - 1986

Fingerprint

Stereochemistry
Cycloaddition
Hydrochloric Acid
X ray crystallography
X Ray Crystallography
Cycloaddition Reaction
Nuclear magnetic resonance
ketene
2,3-dihydrofuran
2-pentanone
Proton Magnetic Resonance Spectroscopy

Cite this

Agathocleous, Demetrios ; Cox, Graham ; Page, Michael I. / Stereochemistry and ring opening of a carbocyclic analogue of a 1-oxapenam. In: Tetrahedron Letters. 1986 ; Vol. 27, No. 14. pp. 1631-1634.
@article{7cbe64eb6d8644d184f218e5a6c07043,
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",
language = "English",
volume = "27",
pages = "1631--1634",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "14",

}

Stereochemistry and ring opening of a carbocyclic analogue of a 1-oxapenam. / Agathocleous, Demetrios; Cox, Graham; Page, Michael I.

In: Tetrahedron Letters, Vol. 27, No. 14, 1986, p. 1631-1634.

Research output: Contribution to journalArticle

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0022626188&partnerID=8YFLogxK

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

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

M3 - Article

VL - 27

SP - 1631

EP - 1634

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 14

ER -