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Structure and Rearrangement Reactions of Bis(organosilyl)(organostannyl)hydroxylamines:  A Joint Theoretical/Experimental Study

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journal contribution
posted on 28.12.2002 by Stefan Schmatz, Christina Ebker, Thomas Labahn, Hermann Stoll, Uwe Klingebiel
O-Lithium-N,N-bis(tert-butyldimethylsilyl)hydroxylamide reacts with chlorotrimethylstannane to give N,O-bis(tert-butyldimethylsilyl)-N-(trimethylstannyl)hydroxylamine (1), the crystal structure of which is presented. The primarily formed N,N-bis(tert-butyldimethylsilyl)-O-(trimethylstannyl)hydroxylamine undergoes a dyotropic rearrangement. This reaction mechanism is corroborated by quantum-chemical calculations (B3LYP), partly employing an effective core potential for tin. The possibility for insertion of a stannyl group has been studied by quantum-chemical calculations. The transition states in the various rearrangement reactions of the bis(organylsilyl)stannylhydroxylamine system are discussed in detail.