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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 13, Number 1
JKCSEZ 13(1)
February 20, 1969 

Studies on Tropolones (Ⅱ) β-Methyltropolone Synthesis and Its γ-Isomer

Tropolone 류에 관한 연구 (Ⅱ) β-Methyltropolone의 합성과 그 γ-이성체
Jae Hu Shim

By the three-step synthesis of alkyltropolone from five-membered cyclopentadiene, as described in Part Ⅰ, methyltropolone has been prepared. From the hydrolysis product of dichloroketene-methylcyclopentadiene cycloadduct, β-(Ⅰ) and γ-methyltropolone (Ⅱ) were separated, with the first predominating, by means of repeated fractional recrystallization and fractional vacuum sublimation. The total yield of these methyltropolones in the hydrolysis step was about 40%. Comparison of this result with those obtained in part Ⅰ revealed the following order as the relative readiness of their preparation: tropolone > methyltropolone > ethyltropolone. The reason for formation of the isomeric (Ⅱ) was discussed by an interpretation of NMR spectrum of cycloadduct in the unsaturation and methylgroup region.
83 - 88
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