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Synthesis and reactivity of polychlorocyclopentanones

L. De Buyck

Laboratory of Organic Chemistry, Faculty of Agricultural Sciences, State University of Gent, Coupure 533, B-9000 Gent (Belgium)

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N. De Kimpe,

N. De Kimpe

Laboratory of Organic Chemistry, Faculty of Agricultural Sciences, State University of Gent, Coupure 533, B-9000 Gent (Belgium)

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R. Verhé,

R. Verhé

Laboratory of Organic Chemistry, Faculty of Agricultural Sciences, State University of Gent, Coupure 533, B-9000 Gent (Belgium)

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D. Courtheyn,

D. Courtheyn

Laboratory of Organic Chemistry, Faculty of Agricultural Sciences, State University of Gent, Coupure 533, B-9000 Gent (Belgium)

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N. Schamp,

N. Schamp

Laboratory of Organic Chemistry, Faculty of Agricultural Sciences, State University of Gent, Coupure 533, B-9000 Gent (Belgium)

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L. De Buyck,

L. De Buyck

Laboratory of Organic Chemistry, Faculty of Agricultural Sciences, State University of Gent, Coupure 533, B-9000 Gent (Belgium)

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N. De Kimpe,

N. De Kimpe

Laboratory of Organic Chemistry, Faculty of Agricultural Sciences, State University of Gent, Coupure 533, B-9000 Gent (Belgium)

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R. Verhé,

R. Verhé

Laboratory of Organic Chemistry, Faculty of Agricultural Sciences, State University of Gent, Coupure 533, B-9000 Gent (Belgium)

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D. Courtheyn,

D. Courtheyn

Laboratory of Organic Chemistry, Faculty of Agricultural Sciences, State University of Gent, Coupure 533, B-9000 Gent (Belgium)

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N. Schamp,

N. Schamp

Laboratory of Organic Chemistry, Faculty of Agricultural Sciences, State University of Gent, Coupure 533, B-9000 Gent (Belgium)

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First published: 1980

https://doi.org/10.1002/bscb.19800891204

Citations: 7

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Abstract

Selective chlorination methods were elaborated for the conversion of cyclopentanone into 2, 2, 5, 5-tetrachloro-, 2, 2, 3, 5, 5-pentachloro- and 2, 2, 3, 3, 5, 5-hexachlorocyclopentanone. Dimethylformamide-hydrogen chloride mixtures served as catalysts for enolization and for dehydrochlorination to chlorinated cyclopentenones.

The reactivity of the polychlorocyclopentanones was tested towards zinc (in acetic acid, methanol or acetone) and towards bases in protic solvents. A number of chlorinated cyclopentenones, substitution products and open chain compounds (Grob elimination) were obtained in good yields.

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N. De Kimpe: “Bevoegdverklaard Navorser” of the Belgian “Nationaal Fonds voor Wetenschappelijk Onderzoek” D. Courtheyn: “Aspirant” of the Belgian “Nationaal Fonds voor Wetenschappelijk Onderzoek”.
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Volume89, Issue12

1980

Pages 1043-1059

Synthesis and reactivity of polychlorocyclopentanones

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Synthesis and reactivity of polychlorocyclopentanones

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