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Penicillin transformations : I. Conversion of a penicillin into a 7-oxo-2,3,4,7-tetrahydro-1,4-thiazepine structure

✍ Scribed by Ödön K.J. Kovacs; Bertil Ekström; Berndt Sjöberg

Book ID
104239360
Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
213 KB
Volume
10
Category
Article
ISSN
0040-4039

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✦ Synopsis

In a recent paper Wolfe and Lee (1) reported the epimerization at C-6 of methyl 6-phthalimidopsnicillanate (I) on treatment with basic reagents such as sodium hydride, potassium t-butoxide, or triethylamine. They suggested a reaction mechanism (I~II+III) involving a $-elimination with rupture of the bond between C-5 and S, but could not substantiate it by isolating or trapping the intermediate thiol structure.

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