Mark Efimovich Vol'pin: The path to science

Polyhalomethanes Combined with Lewis Acids in Alkane Chemistry

“…Previously, based on the fact that both exo - and endo -TMNB form the same products at temperatures from −40 to +10 °C, the structures of esters of trimethylenenorbornane-2-carboxylic acid and trimethylenenorbornane-1-carboxylic acid were attributed to 34 and 35 , respectively 145b. However, a detailed reinvestigation of this question by high resolution 13 C NMR compelled us to dismiss this first attribution.…”

“…The discovery of the superelectrophilic properties of systems containing acyl halides in combination with excess aluminum halides 98-100 has served as the starting point in the search for new superelectrophilic complexes which would provide selective and effective functionalization of alkanes and cycloalkanes, and which would be simultaneously more accessible and more convenient to work with than the complexes based on acyl halides. Testing of a number of systems in which the generation of cations or even dications − seems to be, in principle, possible has led to the novel families of organic , and inorganic − superelectrophiles shown in Figure . With respect to selective functionalization of alkanes and cycloalkanes, we find that among these systems the polyhalomethanes in combination with aluminum halides are particularly interesting.…”