The Diverse Reactivity of Disilenes Toward Isocyanides

Authors

Nada Y. Tashkandi, The University of Western Ontario
Sarah L. McOnie, The University of Western Ontario
Jeremy L. Bourque, The University of Western Ontario
Crispin R.W. Reinhold, Universität Oldenburg
Kim M. Baines, The University of Western Ontario

Document Type

Article

Publication Date

3-4-2019

Journal

Angewandte Chemie - International Edition

Volume

58

Issue

10

First Page

3167

Last Page

3172

URL with Digital Object Identifier

10.1002/anie.201808490

Abstract

The addition of 2,6-dimethylphenyl isocyanide and t-butyl isocyanide to tetramesityldisilene was examined. In both cases, the initially formed product is an iminodisilirane; however, the iminodisiliranes are unstable under the reaction conditions and react with a second equivalent of the isocyanide to give either a 3-silaazetidine or a novel bicyclic double enamine, respectively. Taken together with the previous examples in the literature, the results demonstrate that subtle differences in the steric bulk of the disilene or the electronic effects of the isocyanide can lead to dramatic differences in the reaction pathway.