Abstract
The reaction of carbanions α-to nitriles with tertiary bromoester 1 does not give cyclopropanes, whatever the reaction conditions, while Li enolate of methyl phenylacetate does, in THF or THF-Et 2O. From lithiated aminonitriles 5, in THF-HMPA, the reaction leads to a mixture of S N and S N' products in equal amounts via a radical process. From arylaceto- and propionitriles 4 whatever the conditions, and from methyl phenylacetate enolate 16, either associated to Li in THF-HMPA or to K in THF, S N' anti-Michaël products are predominantly formed via a concerted inner sphere process, showing thus the possibility of a polar-SET mechanistic spectrum from a single electrophilic reagent.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
