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Issue 4, 2014
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Singlet carbenes as mimics for transition metals: synthesis of an air stable organic mixed valence compound [M2(C2)+˙; M = cyclic(alkyl)(amino)carbene]

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Abstract

A cyclic C-bromo-iminium bromide reacts with lithium trimethylsilyl acetylide to afford the title compound 2+˙ in 40% yield. In contrast to other organic mixed valence compounds, this radical cation can be stored in air. Oxidation and reduction of 2+˙ afford the corresponding dication 2++ and neutral cumulene 2, respectively, in good yields.

Graphical abstract: Singlet carbenes as mimics for transition metals: synthesis of an air stable organic mixed valence compound [M2(C2)+˙; M = cyclic(alkyl)(amino)carbene]

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Article information


Submitted
13 Mar 2014
Accepted
24 Mar 2014
First published
25 Mar 2014

Org. Chem. Front., 2014,1, 351-354
Article type
Research Article

Singlet carbenes as mimics for transition metals: synthesis of an air stable organic mixed valence compound [M2(C2)+˙; M = cyclic(alkyl)(amino)carbene]

L. Jin, M. Melaimi, L. L. Liu and G. Bertrand, Org. Chem. Front., 2014, 1, 351
DOI: 10.1039/C4QO00072B

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