334529-34-9Relevant academic research and scientific papers
Iododifluoromethyl alkenes [ICF2CH=CHR]: A labile system generated from 1,1-difluoro-1,3-diiodoalkanes and its trapping with nucleophiles
Guo,Chen
, p. 89 - 96 (2007/10/03)
Treatment of 1,1-difluoro-1,3-diiodoalkanes (ICF2CH2CHIR1, 1) with NEt3 in various solvents or with KF/Al2O3/CH3CN gave no alkenes (ICF2CH=CHR1, 2), whereas with NaOH afforded α,β-unsaturated carboxylic acids, although a signal of 2 in 19F 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 CF2=CHCH(SR)R1 and RSCF2CH=CHR1, whereas the latter affords only ArOCF2CH=CHR1. The nucleophilic substitution of the bromoanalogues, BrCF2CH2CHBrR1 and BrCF2CH=CHR1, has also been investigated. A mechanism involving SN2′ and an allene intermediate is proposed.
