ISSN:
1434-4475
Keywords:
Chloroformate
;
Chloro(di)thioformate acylation
;
5-Amino-1,2,3,4-thiatriazole
;
Trithiadiazapentalenes
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Zusammenfassung Die durch Pyridine katalysierte Acylierung von 5-Amino-1,2,3,4-thiatriazol mit Chlorameisensäureethylester führt zu 3,5-bis-(ethoxycarbonylamino)-1,2,4-thiadiazolen, während mit Chlorthioameisensäureethylester 2,5-bis(phenoxy)-1,6,6a,Δ4-trithia-3,4-diazapentalene erhalten werden. Ohne Pyridin entsteht bei letzterer Reaktion ein wenig stabiles, aber isolierbares Zwischenprodukt: 2-Phenoxy-1-aza-3,4-dithiolium-5-imid. Die Bis(phenoxy)trithiadiazapentalene reagieren leicht mit nukleophilen Reagenzien und tauschen dabei schrittweise eine oder beide Phenoxygruppen aus.
Notes:
Summary Pyridine catalyzed acylation of 5-amino-1,2,3,4-thiatriazole with chloroformates and chlorothioformates afforded 3,5-bis(ethoxycarbonylamino)-1,2,4-thiadiazoles in the former and 2,5-bis(phenoxy)-1,6,6a,Δ4-trithia-3,4-diazapentalenes in the latter case. An unstable, but isolable intermediate 2-phenoxy-1-aza-3,4-dithiolium-5-imide has been found if the chlorothioformate acylation was performed in acetonitrile in the absence of pyridine. The bis(phenoxy)trithiapentalenes are prone to nucleophilic displacement reactions at positions 2 and 5, exchanging in a stepwise manner one or both phenoxy groups. The structures of the compounds described could be inferred from their1H-NMR13C-NMR, and mass spectra and were corroborated by the comparison with the data of authentic and similar derivatives as well as by chemical means.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00808771
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