694-73-5Relevant academic research and scientific papers
Vinyl Carbocations Generated under Basic Conditions and Their Intramolecular C-H Insertion Reactions
Wigman, Benjamin,Popov, Stasik,Bagdasarian, Alex L.,Shao, Brian,Benton, Tyler R.,Williams, Chloé G.,Fisher, Steven P.,Lavallo, Vincent,Houk,Nelson, Hosea M.
supporting information, p. 9140 - 9144 (2019/06/08)
Here we report the surprising discovery that high-energy vinyl carbocations can be generated under strongly basic conditions, and that they engage in intramolecular sp3 C-H insertion reactions through the catalysis of weakly coordinating anion salts. This approach relies on the unconventional combination of lithium hexamethyldisilazide base and the commercially available catalyst, triphenylmethylium tetrakis(pentafluorophenyl)borate. These reagents form a catalytically active lithium species that enables the application of vinyl cation C-H insertion reactions to heteroatom-containing substrates.
Functionalization of saturated hydrocarbons. High temperature bromination of octahydropentalene. Part 19
Günba?, Duygu D.,Algi, Fatih,H?kelek, Tuncer,Watson, William H.,Balci, Metin
, p. 11177 - 11183 (2007/10/03)
The synthesis and thermal bromination of octahydropentalene was studied. The reaction afforded 1a,3a,4b,6b-tetrabromo-1,2,3,4,5,6-hexahydropentalene (14) with remarkable regio- and stereospecificity. The structure of the product was determined by 1H and 13C NMR data and single X-ray structural analysis. The treatment of octahydropentalene with tenfold bromine gave the octabromopentalene derivative. The formation mechanism of the products is discussed.
