INVESTIGADORES
PIRO Oscar Enrique
artículos
Título:
Novel Synthesis of 3,4,4-Trisubstituted Thiadiazolines from 3,4-Diphenyl-1,2,5-Thiadiazole 1,1-Dioxide. Competition with the Intra-Molecular Aryl-Aryl Cyclization of 3,4-Diphenyl-1,2,5-Thiadiazole 1,1-Dioxide
Autor/es:
M. F. ROZAS; M. V. MIRÍFICO; E. J. VASINI; O. E. PIRO; E. E. CASTELLANO
Revista:
SYNTHESIS
Editorial:
Verlag
Referencias:
Año: 2002 vol. 16 p. 2399 - 2403
ISSN:
1414-915X
Resumen:
Abstract3,4-diphenyl-1,2,5-thiadiazole 1,1-dioxide (1) reacted, in the presence of anhydrous AlCl3, with aromatic nucleophiles possessing electron donor substituent groups to give novel (2a-e, scheme 1) 3,4,4-trisubstituted 1,2,5-thiadiazoline 1,1-dioxides in good yield. In the presence of AlCl3, but without the addition of nucleophiles, a slower, but practically quantitative intramolecular cyclization reaction (Scholl reaction1) of 1 to phenanthro [9,10-c]-1,2,5-thiadiazole 1,1-dioxide (3), took place. Both reactions occur through the intermediation of a strong electrophile formed by 1 and AlCl3. Spectral data and structure (through single-crystal X-ray diffraction, with the exception of 2c) were measured for all new compounds.
