137440-79-0Relevant academic research and scientific papers
Reactions of arylthiazylamides with internal and external fluoro electrophiles - Formation of products with unusual structures
Lork, Enno,Mews, Ruediger,Shakirov, Makhmut M.,Watson, Paul G.,Zibarev, Andrey V.
, p. 2123 - 2134 (2007/10/03)
The heteroatom reactivity of the title anions [as (Me2N)3S+ and Cs+ salts] toward both internal and external fluoro electrophiles has been investigated. The intramolecular nucleophilic cyclization of [ArNSN]- (as the cesium salts) bearing at least one ortho fluorine afforded 2,1,3-benzothiadiazoles (e.g. 2a,b), whereas intermolecular condensation with polyfluorinated pyridine and naphthalene afforded Ar-N=S=N-R with R = 4-PyF (4) and R = 2-NpF (8). Further interaction of [ArNSN]- with 4 or 8 proceeded with the transfer of NSN units resulting in (ArN=)2S (5) and [RNSN]-, followed by decomposition (R = 4-PyF) to 4-PyFNH2 (6) or intramolecular cyclization (R = 2-NpF) to the polyfluorinated thiadiazole 9. The compounds of types 4, 5, 8, and 9 have been characterized by single-crystal X-ray diffraction as having both Z,E and Z,Z configurations [8 and 9 as molecular complexes with C10F8 and (Ph-N=)2S (5e), respectively, featuring π-stacking interactions of the arene-polyfluoroarene type]. Besides normal aryl-polyfluoroaryl interactions, the 8·C10F8 complex also displays unusual polyfluoroaryl-polyfluoroaryl π-stacking.
SYNTHESIS OF EXTENDED ACYCLIC AZATHIENES WITH AROMATIC SUBSTITUENTS. III. PHTHALIMIDO GROUP AS THE LEAVING GROUP
Zibarev, A. V.,Miller, A. O.,Shakirov, M. M.,Furin, G. G.
, p. 864 - 872 (2007/10/02)
The use of the phthalimido group as the leaving group makes it possible to obtain asymmetric 1,7-diaryl-1,3,5,7-tetraaza-2,4,6-trithia-1,2,5,6-heptatetraenes, which are not obtainable by the previously known methods.Cesium fluoride in acetonitrile increases the nucleophilicity of the nitrogen atom of the N-trimethylsilyl derivatives of acyclic azathienes and phthalimide.In acetonitrile solution a spontaneous shortening of the sulfur-nitrogen chain of 1,7-bis(trimethylsilyl)-1,3,5,7-tetraaza-2,4,6-trithia-1,2,5,6-heptatetraene takes place.
