TRIMETHYLSILYL AND DIETHYLBORIC DERIVATIVES OF ETHYL N-NITROCARBAMATE

The trimethylsilyl and diethylboron derivatives of ethyl-N-nitrocarbamate were prepared. The former compound was found to exist as an equilibrium mixture of three stereoisomers, i.e., the N- and O-derivatives together with the previously unknown “imide” isomer. A mechanism of the tautomeric rearrangements in the system, involving both the charged ring intramolecular and the dissociative migration of the Si(CH3)3 group is suggested. The latter compound appears to exist in its “imide” form in which the boron atom is coordinated to the carbonyl group oxygen. The pyridine complex of this derivative has the N-isomer structure.