Discovery of Tetrahydrofuran-3-carboxylic acid

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Chemistry is an experimental science, and the best way to enjoy it and learn about it is performing experiments. SDS of cas: 89364-31-8. Introducing a new discovery about 89364-31-8, Name is Tetrahydrofuran-3-carboxylic acid

The reactivity of 2-oxa-6-norbornanediazonium ions (19, 20) conforms to that of the analogous brosylates (7, 11).Photolysis of the tosylhydrazone 17 in aqueous sodium hydroxide yields 2-oxa-exo-6-norbornanol (15) with no endo isomer 22.The deuterium incorporated from D2O/DONa is distributed equally between positions 1 and 6 of 15, suggesting the tricyclic oxonium ion 8 as an intermediate. – After many fortuitous attempts, 2-oxa-exo-5-norbornanol (45a) was prepared from cis-4-hydroxy-2-cyclopentene-1-methanol (41a), a Prins product of cyclopentadiene, by addition of 2-chloroethanol, cyclization of the primary brosylate, and removal of the protecting group with n-butyllithium.The tosylhydrazone 47, obtained via ketone 26, gave 99percent of 45a on irradiation.Deviations from equidistribution of a deuterium label were slight (5-D:4-D = 1.1-1.2).The small effect of the internal oxygen substituent in cation 50 stands in contrast to the much stronger effect of 6-alkoxy groups on 2-norbornyl cations (52).A rationale is provided by the conformation-dependent interaction of alkoxy groups with protonated cyclopropans, as calculated by Schleyer et al.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem