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Acid hydrolysis of 2-iminoperhydrothieno[3, 4-d]-oxazol-5,5-dioxides

✍ Scribed by A. B. Rozhenko; V. I. Slutskii; G. I. Khaskin; E. G. Khil'chevskaya

Book ID
104782066
Publisher
Springer US
Year
1988
Tongue
English
Weight
49 KB
Volume
24
Category
Article
ISSN
0009-3122

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✦ Synopsis

We have found that refluxing 2-iminooxazolidines Ia-c for 5-15 min in aqueous acetic acid readily causes hydrolytic cleavage of the C=N bond and formation of the 2-oxazolidines IIa,c (R 2 = COCH3) in 75~80% yield.

Under the same conditions using hydrochloric acid the C=N bond is cleaved only in the cis-oxazolidines Ic, d, moreover the 3-acetyl group is simultaneously cleaved to form the oxazolidones IIe, f (R 2 = H, yield up to 70%).

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We have performed a product and kinetic study of the hydrolysis of 3,4-diphenyl-1,2,5-thiadiazole-1,l-dioxide in aqueous solution. Benzil and sulfamide are the only products of hydrolysis and are formed in equimolar yields. The kinetic results indicate that a first order law is followed up to 90% c