Perchloro-(dimethylene-1,2-cyclobutanedione) and Its Solvolytic Degradation

Autor: Fujino, Akira, Kusuda, Kousuke, Sakan, Takeo
Zdroj: Bulletin of the Chemical Society of Japan; January 1966, Vol. 39 Issue: 1 p160-164, 5p
Abstrakt: Perchloro-(3,4-dimethylenecyclobutene) has been converted to 1, 3', 3', 4', 4'-pentachloro-2-methoxy-3,4-dimethylenecyclobutene; in some solutions exposed to the air, this then gradually decomposed to perchloro-(dimethylene-1, 2-cyclobutanedione). The further spontaneous degradation of the last compound in an aqueous ethanol solution has also been investigated in order to elucidate the structures of an unstable intermediate (an adduct of ethanol to the carbonyl) and the end product (the hemi-ketal lactone ester). The physical and chemical properties of these compounds have been given and discussed. A possible bicyclic intermediate caused by the interaction between the hydroxyl group and the diagonally-positioned dichloromethylene group in above unstable ethanol adduct has been suggested in the process from the latter compound to the end product.
Databáze: Supplemental Index