Original scientific paper

Cis and trans-4-Oxoazetidine-2-Sulphonic Acid Derivatives; Preparation and X-Ray Structure Determination

Miće Kovačević ; Pliva-Research Institute, Prilaz Baruna Filipovića 89, Zagreb, Croatia
Zinka Brkić ; Pliva-Research Institute, Prilaz Baruna Filipovića 89, Zagreb, Croatia
Zorica Mandić ; Pliva-Research Institute, Prilaz Baruna Filipovića 89, Zagreb, Croatia
Mirjana Tomić ; Pliva-Research Institute, Prilaz Baruna Filipovića 89, Zagreb, Croatia
Marija Luić ; Institute Rudjcr Bošković, P.O.B. 1016, Zagreb, Croatia
Biserka Kojić Prodić ; Institute Rudjcr Bošković, P.O.B. 1016, Zagreb, Croatia

Abstract

Cis and ćrans-4-oxoazetidine-2-sulphonic acid derivatives were prepared starting from penicillanate sulphoxides (1) and (4). The methylsulphonates (5), (7), (8) and (9) were formed by oxidation of 4-oxoazetidine-2-sulphinates (2), (3), and (6). Generally, 4-oxoazetidine-2-sulphonates were labile entities and hydrolyzed under mild conditions into sulphonic acids. These were isolated as acids (12) and salts (10), (11) and (14). The conformational isomers of the sulphonate (9a) were detected by 'H NMR spectroscopy and confirmed by variable temperature experiments. X-Ray structure analyses of 9a were performed but there wasn’t any evidence for intramolecular hydrogen bonding.

Keywords

Hrčak ID:

137140

URI

https://hrcak.srce.hr/137140

Publication date:

29.1.1993.

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