Abstract
Treatment of 1,1-difluoro-1,3-diiodoalkanes (ICF 2CH 2CHIR 1, 1) with NEt 3 in various solvents or with KF/Al 2O 3/CH 3CN gave no alkenes (ICF 2CHCHR 1, 2), whereas with NaOH afforded α,β-unsaturated carboxylic acids, although a signal of 2 in 19 F NMR spectroscopy could be observed momentarily sometimes. However, the labile 2 can be trapped either with thiolate or phenoxide ions. The former reaction gives a mixture of CF 2CHCH(SR)R 1 and RSCF 2CHCHR 1, whereas the latter affords only ArOCF 2CHCHR 1. The nucleophilic substitution of the bromoanalogues, BrCF 2CH 2CHBrR 1 and BrCF 2CHCHR 1, has also been investigated. A mechanism involving S N2′ and an allene intermediate is proposed.
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.
