The mechanistic study and synthetic applications of the base treatment in the ozonolytic reactions

Article abstract of DOI:10.1016/0040-4020(95)98699-I

The E1cb mechanism is the overwhelming process in the reaction of bases and ozonides. As a quenching agent in the ozonolysis of a variety of alkenes, the reactions involving triethylamine often gave better yields and proceeded faster than those involving methyl sulfide. On the other hand, in the presence of 4 A molecular sieves, the secondary amines reacted with mono- and 1,1-di-substituted ozonides to afford the reductive amination products in high yields. The formation of ammonium formate in the reaction mixture also supported the E1cb mechanism in the reaction of ozonide and amine.