Dichloroacetyl chloride → Bicyclo[4.2.0]oct-2-en-7-one

HRID 1982494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1982494
[CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.Cl[CH:8](Cl)[C:9](Cl)=[O:10]>[Zn].C(O)(=O)C>[CH:2]12[CH2:8][C:9](=[O:10])[CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3]2

Komponenten

5

Edukt 2

HCID 6593Dichloroacetyl chlorideHCID 116051,3-Cyclohexadiene

Produkt 1

HCID 12507350Bicyclo[4.2.0]oct-2-en-7-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

The starting material is prepared by the treatment of 1,3-cyclohexadiene with dichloroacetyl chloride, followed by dechlorination with zinc and acetic acid of the resulting adduct to give bicyclo[4,2,0]-oct-2-en-7-one. This compound is subjected to Baeyer-Villiger oxidation to give 7-oxabicyclo[4,3,0]non-2-en-8-one which is treated with thallium (III) nitrate under carefully controlled conditions to give 6-formyl-2-oxabicyclo[3,3,0]octane-3-one having properties identical with those reported by Corey and Ravindranathan, Tetrahedron Letters, 1971, 4753.

Quellen und Nachweise

ORD-Eintrag
ord-45b7b72e162640208231819c682eee35
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04596823

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