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Synfacts 2016; 12(06): 0579
DOI: 10.1055/s-0035-1562150
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

All-Carbon Carbodicarbene

Contributor(s):
Timothy M. Swager
,
Qifan Zhang
Pranckevicius C, Liu L, Bertrand G, Stephan DW * University of California San Diego, La Jolla, USA and University of Toronto, Canada
Synthesis of a Carbodicyclopropenylidene: A Carbodicarbene Based Solely on Carbon.

Angew. Chem. Int. Ed. 2016;
55: 5536-5540
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Publication History

Publication Date:
17 May 2016 (online)

 
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Key words

carbodicarbenes - bent allenes - carbon donors - gold complexes

Significance

The authors present the first carbo­dicarbene stabilized by two cyclopropenylidenes. Compound 3 is made by deproto­nation of the corresponding triafulvene cyclopropenium salt and is characterized by NMR at –60 °C. The divalent electron-donating property of the center carbon on 3 is confirmed by generating main-group and transition-metal complexes.


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Comment

A carbenoid carbon is usually stabilized by amino groups through charge delocalization. Herein the authors use a phenyl group to serve a similar purpose and the carbodicarbene, which is based solely on carbon without any heteroatom, is very impressive. The stable complexes 4–6 are all characterized by single-crystal X-ray diffraction.


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