Add time:08/23/2019         Source:sciencedirect.com

Ozonolysis of α-terpineol (1) then steam distillation in presence of acid gives the known 4-isopropylidenecyclopentenyl methyl ketone (4). This is oxidized in air to 4-(1-hydroperoxy-1-methylethyl)-1,3-cydopentadienyl methyl ketone (10), a compound frequently reacting as if it were one of the elusive dimethylfulvene epoxides. It is converted by silica gel to two dimers (12, 13) of 2-acetyl-6,6-dimethylfulvene epoxide (19). Catalytic reduction of the dimers occurs mostly by exo addition of hydrogen to the conjugated double bond, and thermolysis of the dimers yields 4-acetyl-6,6-dimethylcyclohexa-2, 4-dienone (20). With triphenylphosphine the hydroperoxide (10) yields two [6 + 4] dimers of 2-acetyl-6,6-dimethylfulvene (26). This is the first reported isolation of [6 + 4] dimers of a fulvene. The hydroperoxide (10) adds diazomethane to give an unstable pyrazoline (28); this pyrazoline loses nitrogen to yield a single isomer XXX. 5-acetyl-3' ,3'-dimethylbicyclo[3.1.0] hex-3-ene-2-spiro-2'-oxirane (29). Catalytic hydrogenation of the latter involves ring opening of the epoxide.

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