B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>- and HB(C<sub>6</sub>F<sub>5</sub>)<sub>2</sub>-mediated transformations of isothiocyanates
Malte Fischer, Marc Schmidtmann
Abstract
This contribution reports on the reactivity of isothiocyanates towards the boranes B(C6F5)3 and HB(C6F5)2. The reactions of alkyl-substituted isothiocyanates with B(C6F5)3 were found to result in rearrangement reactions to yield stable thiocyanate-B(C6F5)3 adducts. Treatment of isothiocyanates with HB(C6F5)2 leads to 1,2-hydroboration and thus, B,N,C,S heterocycles are formed, which react further under non-inert conditions. Hydrolysis of the hydroboration products leads to a new access to thioformamides.
Topics & Concepts
ChemistryCrystallographyOrganoboron and organosilicon chemistrySynthesis and characterization of novel inorganic/organometallic compoundsFluorine in Organic Chemistry