Reactions of silamorpholinones and acylsilamorpholines with electrophilic reagents. X-ray structure of products including a pentacoordinated silicon compound

Shipov, Aleksandr G.; Kramarova, Evgeniya P.; Mamaeva, Elizaveta A.; Oksana, A. Zamyshlyaeva; Negrebetskii, Vadim V.; Ovchinnikov, Yuri E.; Pogozhikh, Sergey A.; Bassindale, Alan R.; Taylor, Peter G. and Baukov, Yuri I. (2001). Reactions of silamorpholinones and acylsilamorpholines with electrophilic reagents. X-ray structure of products including a pentacoordinated silicon compound. Journal of Organometallic Chemistry, 620(1-2) pp. 139–149.

DOI: https://doi.org/10.1016/S0022-328X(00)00821-4

Abstract

Reactions of 2-sila-5-morpholinones, 4-acyl-2-silamorphoiines and 4-acyl-2,6-disilamorpholines with electrophilic reagents generally lead to the opening of the sila- or disilacycle by cleavage of the Si-O bond with subsequent rearrangement to form five-membered chelate derivatives where the amide oxygen atoms coordinate with the silicon to form pentacoordinate silicon species. Multinuclear NMR spectroscopy and X-ray diffraction studies were used for structural investigation of the products. 4-Acyl-2,6-disilamorpholines initially form adducts with strong acids where the amide oxygen is protonated by the acid as demonstrated by X-ray crystallography.

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