Synthesis of a Carbodicyclopropenylidene: A Carbodicarbene based Solely on Carbon

Conor Pranckevicius; Liu Leo Liu; Guy Bertrand; Douglas W Stephan

doi:10.1002/anie.201600765

Synthesis of a Carbodicyclopropenylidene: A Carbodicarbene based Solely on Carbon

Angew Chem Int Ed Engl. 2016 Apr 25;55(18):5536-40. doi: 10.1002/anie.201600765. Epub 2016 Mar 30.

Authors

Conor Pranckevicius¹, Liu Leo Liu², Guy Bertrand², Douglas W Stephan³

Affiliations

¹ Department of Chemistry, University of Toronto, Toronto, ON, M5S 3H6, Canada.
² Joint UCSD-CNRS Research Chemistry Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California San Diego, La Jolla, CA, 92093-0343, USA.
³ Department of Chemistry, University of Toronto, Toronto, ON, M5S 3H6, Canada. dstephan@chem.utoronto.ca.

PMID: 27028936
DOI: 10.1002/anie.201600765

Abstract

The first carbodicarbene stabilized by flanking cyclopropenylidenes is reported. Tetraphenylcarbodicyclopropenylidene (2) is accessed by deprotonation of the corresponding triafulvene cyclopropenium salt, and has been spectroscopically characterized in [D8 ]THF solution at -60 °C. Main-group and transition-metal complexes of 2 have been accessed, and have revealed the high sigma donating ability, and exclusive η(1) binding of this neutral all carbon ligand. Variable temperature NMR spectroscopy studies reveal varying degrees of free rotation in the flanking cyclopropenylidene groups of 2 in its coordination compounds.

Keywords: bent allenes; carbodicarbenes; carbon donors; carbones; gold complexes.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't