One pot conversion of benzophenone imine into the relevant 2-aza-allenium.

Authors :: Bortoluzzi M
Funaioli T
Marchetti F
Pampaloni G
Pinzino C
Zacchini S
Source :: Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2016 Dec 22; Vol. 53 (2), pp. 364-367.
Publication Year :: 2016
Abstract: Interaction of common imines with WCl <subscript>6</subscript> in organic solvents revealed very unusual features in the context of imine chemistry. Ph <subscript>2</subscript> C[double bond, length as m-dash]NH was converted in one pot into the 2-aza-allenium species [Ph <subscript>2</subscript> C[double bond, length as m-dash]N[double bond, length as m-dash]CPh <subscript>2</subscript> ] <superscript>+</superscript> via N <subscript>2</subscript> release, with [Ph <subscript>2</subscript> C[double bond, length as m-dash]NH <subscript>2</subscript> ] <superscript>+</superscript> being a co-product. PhCH[double bond, length as m-dash]N <superscript>t</superscript> Bu underwent C-H bond activation resulting in the formation of [C[triple bond, length as m-dash]N] containing derivatives, together with [PhCH[double bond, length as m-dash]NH <superscript>t</superscript> Bu] <superscript>+</superscript> .