Unexpected formation of 2,1-benzisothiazol-3-ones from oxathiolano ketenimines: a rare tandem process.
A rare one-pot reaction, a tandem [1,5]-H shift/1,5 electrocyclization/[3 + 2] cycloreversion process, leading from N-[2-(1,3-oxathiolan-2-yl)]phenyl ketenimines to 1-(beta-styryl)-2,1-benzisothiazol-3-ones and ethylene, is disclosed and mechanistically unraveled by means of a computational DFT study. The two latter stages of the tandem process are calculated to occur in a single mechanistic step via a transition structure of pseudopericyclic characteristics.
Alajarin
Mateo
M
Departamento de Quimica Organica, Facultad de Quimica, Universidad de Murcia, Campus de Espinardo, 30100 Murcia, Spain. alajarin@um.es
Bonillo
Baltasar
B
Sanchez-Andrada
Pilar
P
Vidal
Angel
A
Bautista
Delia
D