The addition of nitriles to tetramesityldisilene: A comparison of the reactivity between surface and molecular disilenes

Authors

Julie A. Hardwick, The University of Western Ontario
Kim M. Baines, The University of Western OntarioFollow

Document Type

Article

Publication Date

12-18-2015

Journal

Chemistry - A European Journal

Volume

21

Issue

6

First Page

2480

Last Page

2488

URL with Digital Object Identifier

10.1002/chem.201405780

Abstract

The addition of acetonitrile, propionitrile, and phenylacetonitrile to tetramesityldisilene (Mes Si=SiMes ) 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 Si=SiMes and the Si(100)-2 x 1 surface was made both in terms of the types of adducts formed and their reactivity. Some insights into the surface chemistry are offered. 2 2 2 2