Synthesis 2012; 44(20): 3191-3196
DOI: 10.1055/s-0032-1317136
paper
© Georg Thieme Verlag Stuttgart · New York

Catalyst-Free Amidation of Trimethylsilyl Ketene Imines with Isocyanates

Wenling Qin
a   ISOF-CNR Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy, Fax: +39(051)2099456   Email: mauro.panunzio@unibo.it
,
Sha Long
a   ISOF-CNR Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy, Fax: +39(051)2099456   Email: mauro.panunzio@unibo.it
,
Mauro Panunzio*
a   ISOF-CNR Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy, Fax: +39(051)2099456   Email: mauro.panunzio@unibo.it
,
Alessandro Bongini
b   Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy
› Author Affiliations
Further Information

Publication History

Received: 03 July 2012

Accepted after revision: 27 July 2012

Publication Date:
21 August 2012 (online)


Abstract

A catalyst-free method for the amidation of N-trimethylsilyl ketene imines using isocyanates is reported. A working hypothesis on the reaction pathway includes silatropism from the ketene nitrogen to the isocyanate oxygen as the driving force of the process.