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N ‐Germyl derivatives of sulfacetamide and ortho ‐(sulfonamido)phenylamines: characterization of N ‐[ o ‐( N ′, N ′‐dimethylsulfonamido)phenyl]‐ N ‐dimesitylgermaimine
Author(s) -
Chazalette C.,
Khallaayoun A.,
RivièreBaudet M.,
El Baz F.
Publication year - 2003
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.406
Subject(s) - chemistry , dimethylamine , dehydrohalogenation , thermal decomposition , decomposition , nitrogen , medicinal chemistry , organic chemistry , catalysis
Triethylgermylation of sulfacetamide occurs on the sulfonamido nitrogen in competition with the 1,2 addition of the starting triethylgermyl dimethylamine on the carbonyl group. Thermal decomposition in the presence of dimethylamine yields N ‐triethylgermylsulfanilamide. Stable 1:1 sulfacetamide–DBU and 1:1 sulfacetamide–Et 3 N complexes were isolated and fully characterized in the course of dehydrochlorination reactions. o ‐Sulfonamidophenylamine yields N,N ′‐bis‐triethylgermylated derivatives, whereas o ‐( N,N ‐dimethylsulfonamido)phenylamine leads to monogermylated compounds. The N ‐dimethylaminodimesitylgermyl derivative is thermally stable. Dehydrohalogenation of the N ‐dimesitylfluorogermyl compound leads to the thermally stable but water sensitive N ‐[ o ‐( N ′, N ′‐dimethylsulfonamido)phenyl]‐ N ‐dimesitylgermaimine. Copyright © 2003 John Wiley & Sons, Ltd.