It is shown that N-phenyl-substituted isothiazolium salts 2/3a–e with active 5-methyl or 5-methylene groups can easily be obtained by reaction of β-thiocyanatovinylaldehydes 1 and substituted anilines. Based on a wide variety of isothiazolium salts accessible in that way, a study of their various reaction products, e.g. 1,6-diphenyl-substituted thiadiazapentalenes 4a–d, 5a–j and special spiro compounds 6, and the influence of donor and acceptor substituents becomes possible. The structure of the basic skeleton of the thiadiazapentalenes was confirmed by X-ray analysis and ab initio MO calculations. Some mechanistic aspects are supported by the MO results.
Base‐induced reactions of isothiazolium salts with active 5‐methyl or 5‐methylene groups
CIMIRAGLIA, Renzo;
1995
Abstract
It is shown that N-phenyl-substituted isothiazolium salts 2/3a–e with active 5-methyl or 5-methylene groups can easily be obtained by reaction of β-thiocyanatovinylaldehydes 1 and substituted anilines. Based on a wide variety of isothiazolium salts accessible in that way, a study of their various reaction products, e.g. 1,6-diphenyl-substituted thiadiazapentalenes 4a–d, 5a–j and special spiro compounds 6, and the influence of donor and acceptor substituents becomes possible. The structure of the basic skeleton of the thiadiazapentalenes was confirmed by X-ray analysis and ab initio MO calculations. Some mechanistic aspects are supported by the MO results.I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
