Cyclodienones. Part 8. Hydrolysis of 5-Oxo-2,4-di-t-Butylcyclopenta-1,3-dienecarbonitrile

DOI: 10.1039/P19820000243

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Journal of the Chemical Society. Perkin transactions I p. 243 - 246 (1982)

Update date:2022-08-05

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Authors:

Tashiro, Masashi

Sakamoto, Naoya

Fukata, Gouki

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Article abstract of DOI:10.1039/P19820000243

The acid-catalysed hydrolysis of 5-oxo-2,4-di-t-butylcyclopenta-1,3-dienecarbonitrile (2) gave the novel products 3,3a,6,6a-tetrahydro-3,3,3a-trimethyl-5-t-butyl-1H-cyclopentafuran-1,6-dione (5), 4,5-dimethyl-7-t-butyl-bicyclo<3.3.0>octa-3,6-diene-2,8-dione (6), and 2-carbamoyl-5-isopropylidene-3-methylcyclopent-2-enone (7), but not the expected carboxylic acid (3).Treatment of compound (5) with 10percent NaOH followed by acidification with 10percent HCl gave, in 88percent yield, the unexpected 2-methyl-5-oxo-4-t-butylcyclopent-1-enecarboxylic acid (8) which, on termolysis, gave 3-methyl-5-t-butylcyclopent-2-enone (9) and 4-methyl-2-t-butyl-cyclopent-3- enone (10) in 51 and 36percent yields, respectively.The base catalysed hydrolysis of compounds (2) has also been attempted.

Full text of DOI:10.1039/P19820000243

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