Abstract
A study exploring halofluorination and fluoroselenation of some cyclic olefins, such as diesters, imides, and lactams with varied functionalization patterns and different structural architectures is described. The synthetic methodologies were based on electrophilic activation through halonium ions of the ring olefin bonds, followed by nucleophilic fluorination with Deoxo-Fluor®. The fluorine-containing products thus obtained were subjected to elimination reactions, yielding various fluorine-containing small-molecular entities.
Highlights
The effects of fluorine on lipophilicity, metabolism, binding, and bioavailability are often beneficial [1,2,3,4,5,6,7,8,9]
The first substrate, the cyclohexene diester-1, has a twofold rotational symmetry, that is the formation of only a single halonium ion intermediate is possible
Novel fluorine-containing, functionalized smallmolecular scaffolds have been accessed through halofluorination or selenofluorination protocols
Summary
The effects of fluorine on lipophilicity, metabolism, binding, and bioavailability are often beneficial [1,2,3,4,5,6,7,8,9]. Scheme 2: Halofluorination reactions of the trans-diester (rac)-1. Both bromo- and iodofluorination of 7 yielded a mixture of two isomeric halofluorinated products for which the separation failed (Scheme 5). Scheme 5: Halofluorination reactions of the cis-tetrahydrophthalic imide derivative 7.
Sign-in/Register to view highlights & summary 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.
