10.1016/j.tetlet.2006.04.097
The research focuses on the synthesis of substituted 3-furan-2(5H)-ones, which are structural motifs found in numerous bioactive natural products. The methodology involves a Diels–Alder sequence using anthracene and maleic anhydride to form a lactone, which upon deprotonation and electrophilic quenching, yields α-substituted lactones. Key reactants include anthracene, maleic anhydride, sodium borohydride, and various electrophiles such as methyl iodide, allyl iodide, butenyl bromide, benzyl bromide, tributyltin chloride, diethyl chlorophosphate, and chlorotrimethylsilane. The experiments utilize techniques like flash vacuum pyrolysis (FVP) to convert alkylated lactones into 3-substituted furan-2(5H)-ones. The study also explores the challenges and limitations of using cyclopentadiene in such reactions and proposes an alternative route to overcome these issues. Analytical techniques such as 13C NMR and IR spectroscopy were employed to confirm the structure and successful functionalization of the synthesized compounds.
10.1016/S0040-4039(00)87332-3
The research focuses on the preparation and synthetic application of (diethylphosphinyl)difluoromethyllithium, a reagent derived from the reaction of lithium diisopropylamide with diethyl difluoromethylphosphonate. The purpose of this study is to introduce difluoromethylene or difluoromethyl units into various electrophiles, which can lead to a remarkable enhancement of biological activity in organic compounds, as observed in the case of halogenated pesticides like decamethrin and NRDC-1821. The researchers successfully synthesized a range of compounds with difluoro-methylene or difluoromethyl groups from ketones and aldehydes, using this reagent. They found that the reaction yields varied depending on the electrophiles used, with some achieving high yields such as Me3SiCl (87%) and EtBr (82%), while others like CH2=CHCH2Br resulted in lower yields (23%). The study also explored the conversion of intermediate adducts into 1,1-difluoro olefins using the Wadsworth-Emmons reaction. The chemicals used in this process include diethyl difluoromethyl phosphonate, lithium diisopropylamide, and various electrophiles such as Me3SiCl, n-Bu3SnCl, (EtO)2P(O)Cl, and EtBr, among others. The conclusions drawn from the research indicate that while the procedure is generally applicable to various ketones and aldehydes, certain functional groups like nitro or pyridine rings did not yield the desired products and sometimes led to rearrangements.