Abstract
The iodine-transfer addition of methyliodomalonodinitrile (1) to several dialkyl-substituted olefins is reported. The iodine-transfer reaction to the acyclic nonconjugated radical intermediates often results in selective product formation due to 1,2-asymmetric induction. The level of diasterselectivity depends on the size of the alkyl substituent on the radical. Tertiary alkyl groups give high syn selectivity, secondary groups lead to a moderate syn selectivity, and primary groups show completely unselective reactions. To explain the stereochemical outcome, a new steric model of the 1 Bu-substituted radical 5e is introduced on the basis of AM1 calculations and EPR data
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: 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.