THE USE OF ACYL DERIVATIVES OF N-HYDROXY-2-THIOPYRIDONE IN A SIMPLE SYNTHESIS OF PYRROLIDINES AND TETRAHYDROFURANS

Article abstract of DOI:10.1016/S0040-4039(00)99175-5

Photolysis of the N-hydroxy-2-thiopyridone derivatives of 3-N-acetylallylamino, 3-N,N-diallylamino and 3-allyloxy-propionic acids gave cleanly derivatives of N-acetyl-3-methylpyrrolidine, N-allyl-3-methylpyrrolidine and of 3-methyltetrahydrofuran respectively.The corresponding reaction with 3-allylthiopropionic acid afforded a radical which fragmented to ethylene and the allylthio radical without cyclization.