2-(Trimethylsiloxy)phenyl isocyanide (1) reacts at
−60 °C with triphenylborane to form
the isocyanide adduct (2-(trimethylsiloxy)phenyl
isocyanide)−triphenylborane (2). Upon
desilylation in MeOH with a catalytic amount of KF at −30 °C
2 is converted into the ylidene
adduct (1,2-dihydrobenzoxazol-2-ylidene)−triphenylborane
(3). The X-ray crystal structures
of 2 and 3 are reported. When it is heated,
2 dimerizes to give
1,4-bis(2-(trimethylsiloxy)phenyl)-2,2,3,5,5,6-hexaphenyl-2,5-dibora-2,5-dihydropyrazine
(4). Si−O bond cleavage leads
to
1,4-bis(2-hydroxyphenyl)-2,2,3,5,5,6-hexaphenyl-2,5-dibora-2,5-dihydropyrazine
(5). Attempts to induce formation of a boron-bridged diylidene complex
via attack of the hydroxyl
oxygens in 5 at the pyrazine carbon atoms failed.
Instead, complex 6, containing one
bridging
N,O-ylidene ligand, was obtained by partial hydrolysis of 5.
The molecular structure of 6,
which crystallizes with one molecule of methanol and acetone each per
formula unit, is
reported.