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The Addition of Nitriles to Tetramesityldisilene: A Comparison of the Reactivity between Surface and Molecular Disilenes
Author(s) -
Hardwick Julie A.,
Baines Kim M.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405780
Subject(s) - propionitrile , reactivity (psychology) , acetonitrile , chemistry , adduct , ketenimine , nitrile , tautomer , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology
The addition of acetonitrile, propionitrile, and phenylacetonitrile to tetramesityldisilene (Mes 2 SiSiMes 2 ) was examined. In general, 1,2,3‐azadisiletines and the tautomeric enamines were formed, although a ketenimine was formed as the major product in the addition of phenylacetonitrile to the disilene. In the presence of LiCl, the mode of addition changed for both acetonitrile and propionitrile: insertion into the α‐CH bond of acetonitrile and/or formation of the formal HCN adduct was observed. Preliminary investigations of the reactivity of the nitrile adducts are also reported. A comparison between the reactivity of nitriles with Mes 2 SiSiMes 2 and the Si(100)‐2×1 surface was made both in terms of the types of adducts formed and their reactivity. Some insights into the surface chemistry are offered.