Issue 2, 2017
From the journal:

Chemical Communications

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

Marco Bortoluzzi,*a   Tiziana Funaioli,b   Fabio Marchetti, ORCID logo *b   Guido Pampaloni,b   Calogero Pinzinoc  and  Stefano Zacchinid  

* Corresponding authors

a University Ca' Foscari Venezia, Dipartimento di Scienze Molecolari e Nanosistemi, Via Torino 155, I-30170 Mestre (VE), Italy
E-mail: markos@unive.it
Web: http://www.unive.it/data/people/5591286
Tel: +39 041 234 8561

b University of Pisa, Dipartimento di Chimica e Chimica Industriale, Via Moruzzi 13, I-56124 Pisa, Italy
E-mail: fabio.marchetti1974@unipi.it
Web: http://www.dcci.unipi.it/fabio-marchetti.html
Tel: +39 050 2219245

c ICCOM-CNR, Area della Ricerca, Via G. Moruzzi 1, I-56124 Pisa, Italy

d University of Bologna, Dipartimento di Chimica Industriale “Toso Montanari”, Viale Risorgimento 4, I-40136 Bologna, Italy

Abstract

Interaction of common imines with WCl6 in organic solvents revealed very unusual features in the context of imine chemistry. Ph2C[double bond, length as m-dash]NH was converted in one pot into the 2-aza-allenium species [Ph2C[double bond, length as m-dash]N[double bond, length as m-dash]CPh2]+via N2 release, with [Ph2C[double bond, length as m-dash]NH2]+ being a co-product. PhCH[double bond, length as m-dash]NtBu 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]NHtBu]+.

Graphical abstract: One pot conversion of benzophenone imine into the relevant 2-aza-allenium

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Article information

DOI
https://doi.org/10.1039/C6CC08702G
Article type
Communication
Submitted
29 Oct 2016
Accepted
01 Dec 2016
First published
09 Dec 2016

Chem. Commun., 2017,53, 364-367

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

M. Bortoluzzi, T. Funaioli, F. Marchetti, G. Pampaloni, C. Pinzino and S. Zacchini, Chem. Commun., 2017, 53, 364 DOI: 10.1039/C6CC08702G

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