Addition of nitromethane to a disilene and a digermene: Comparison to surface reactivity and the facile formation of 1,3,2-dioxazolidines

Authors

Nada Y. Tashkandi, The University of Western Ontario
Frederick Parsons, The University of Western Ontario
Jiacheng Guo, The University of Western Ontario
Kim M. Baines, The University of Western OntarioFollow

Document Type

Article

Publication Date

1-26-2015

Journal

Angewandte Chemie - International Edition

Volume

54

Issue

5

First Page

1612

Last Page

1615

URL with Digital Object Identifier

10.1002/anie.201409707

Abstract

The addition of nitromethane to tetramesityldisilene and tetramesityldigermene leads to the formation of the novel 1,3,2,4,5-dioxazadisil- and digermolidine ring systems, respectively. The 1,3,2,4,5-dioxazadisilolidine isomerizes to the 1,4,2,3,5-dioxazadisilolidine ring system, whereas the 1,3,2,4,5-dioxazadigermolidine undergoes ring opening to the isomeric oxime. The preferential formation of the 1,3,2,4,5-dioxazadisilolidine, and its rearrangement to a 1,4,2,3,5-dioxazadisilolidine, provides support for the suggested reaction pathway between nitromethane and the Si(100) 2×1 reconstructed surface.