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The Diverse Reactivity of Disilenes Toward Isocyanides
Author(s) -
Tashkandi Nada Y.,
McOnie Sarah L.,
Bourque Jeremy L.,
Reinhold Crispin R. W.,
Baines Kim M.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808490
Subject(s) - isocyanide , steric effects , chemistry , reactivity (psychology) , enamine , ugi reaction , bicyclic molecule , medicinal chemistry , stereochemistry , photochemistry , computational chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
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.