81602-16-6Relevant academic research and scientific papers
1,3,2-Oxazaphospholidine-2-thiones from (+)-Norephedrine: Stereospecific Ring Opening, Possibly by an Elimination-Addition Mechanism
Hall, C.Richard,Inch, Thomas D.,Williams, Nancy E.
, p. 639 - 644 (2007/10/02)
1,3,2-Oxazaphospholidine-2-thiones derived from (+)-norephedrine react with alkoxide to give a product of kinetic control, formed by endocyclic P-O cleavage with inversion of configuration, and one of thermodynamic control, formed by endocyclic P-N cleavage also with inversion of configuration.It is suggested that the product of kinetic control is formed by an elimination-addition process involving a metaphosphorimidate intermediate, and that of thermodynamic control by a mechanism involving nucleophilic attack opposite endocyclic nitrogen.
