D. Pole, P. Sharma, J. Warkentin
Jul 1, 1996
Citations
0
Influential Citations
5
Citations
Journal
Canadian Journal of Chemistry
Abstract
Methoxy-(2-trimethylsilyl)ethoxycarbene reacts with two equivalents of dimethyl acetylene dicarboxylate, methyl propiolate, phenyl acetylene, or phenyl isocyanate without rearrangement of the carbene group. N-Phenylmaleimide captures the carbene with I: 1 -stoichiometry. The structure of the product implies that a migration of the trimethylsilylethyl group from oxygen to carbon accompanies that reaction. A mechanism for that complex rearrangement is proposed. Phenol and tert-butyl alcohol afford the orthoformates expected from overall insertion of the carbene into the OH bond.