The reaction of 2-methyl-2-nitrosopropane and related species with organoboranes: a ready cis-elimination of alkene from trialkylboranes

Abstract

2-Methyl-2-nitrosopropane undergoes a remarkably ready reaction at room temperature with a trialkylborane to bring about the elimination of one B-alkyl group as alkene. The reaction involves stereospecific cis-elimination and may have synthetic utility.

Di-t-alkyl nitroxides react only slowly with trialkylboranes at ambient temperatures. Diethylhydroxylamine and cyclohexanone oxime react rapidly at 35° with trialkylboranes to cleave off one alkyl group as alkane.