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Tetrahedron | 1984

The meta photocycloaddition of anisole to oxa- and dioxa-cyclopentenes and to ethyl vinyl ether

A. W. H. Jans; B. van Arkel; J.J. van Dijk-Knepper; H. Mioch; J. Cornelisse

Abstract The meta photocycloaddition of anisole to 2,3- and 2,5-dihydrofuran, 1,3-dioxole and ethyl vinyl ether is described. The NMR data of the adducts are presented. The reaction yields mixtures of endo and exo adducts. The endo/exo ratio is strongly influenced by the presence of one or two oxygen atoms next to the double bond of the alkene. A mechanism is presented in which a zwitterionic intermediate is formed from the excited anisole and the alkene.


Tetrahedron Letters | 1985

The meta photocycloaddition of anisole and benzonitrile to 1,3-dioxol-2-one

E.M. Osselton; C.P. Eyken; A. W. H. Jans; J. Cornelisse

Abstract The meta photocycloadditions of benzonitrile and anisole to 1,3-dioxol-2-one both yield two major products. In both cases the adducts are those which would be expected if some form of polar species were to develop along the reaction pathway. The absence of exo adducts in the case of benzonitrile and 1,3-dioxol-2-one is discussed.


Tetrahedron Letters | 1982

The meta-photocycloaddition of ethylvinylether to 3-methylanisole and 3-fluoroanisole

A. W. H. Jans; B. van Arkel; J.J. van Dijk-Knepper; J. Cornelisse

Abstract Photoaddition of ethylvinylether to 3-methylanisole yields six derivatives of 1-methoxytricyclo[3.3.0.02,8]oct-3-ene. Four of the adducts have the ethoxy group in an endo position. Products in which the methyl group is at position 4 are favoured. Photoaddition of ethylvinylether to 3-fluoroanisole yields three isomeric adducts, to endo and one exo.


Tetrahedron Letters | 1982

Photocycloaddition of ethylvinylether and cyclopentene to 3.5-dimethylanisole

A. W. H. Jans; J.J. van Dijk-Knepper; J. Cornelisse; C. Kruk

Abstract Photocycloadition of ethylvinylether and cyclopentene to 3,5-dimethylanisole yields derivatives of 1-methoxy-2, 4-dimethyltricyclo [3.3.0.0 2,8 ]oct-3-ene in which the substituents at positions 6 and/or 7 are endo. Structural proofs are based on 250 MHz 1 H and 62.9 MHz 13 C NMR spectra.


Recueil des Travaux Chimiques des Pays-Bas | 2010

The meta-photocyloaddition of cyclopentene to anisole

A. W. H. Jans; J.J. van Dijk-Knepper; J. Cornelisse


Magnetic Resonance in Chemistry | 1982

1H and 13C NMR studies on 1‐methoxy‐endo‐tetracyclo[6.3.0.02,11.03,7]undec‐9‐ene

A. W. H. Jans; J. Lugtenburg; J. Cornelisse; C. Kruk


Magnetic Resonance in Chemistry | 1985

Proton NMR study of methyl‐ and fluoro‐substituted 6‐ and 7‐ethoxy‐1‐methoxytricyclo[3.3.0.02,8]oct‐3‐enes

A. W. H. Jans; B. van Arkel; E. M. Osselton; J. Cornelisse


Magnetic Resonance in Chemistry | 1985

Two-dimensional INADEQUATE 13C NMR Study on Vitamin D3

C. Kruk; A. W. H. Jans; J. Lugtenburg


Magnetic Resonance in Chemistry | 1985

Application of two‐dimensional correlated NMR techniques to the structure elucidation of 1‐methoxy‐endo‐tetracyclo[6.3.0.02,11.03,7]‐ undec‐9‐ene

C. Kruk; A. W. H. Jans; J. Cornelisse; J. Lugtenburg


ChemInform | 1985

THE META PHOTOCYCLOADDITION OF ANISOLE AND BENZONITRILE TO 1,3-DIOXOL-2-ONE

E. M. Osselton; C. P. Eyken; A. W. H. Jans; J. Cornelisse

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C. Kruk

University of Amsterdam

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