Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 27th March 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 90, 2016
Previous Article Next Article

Cyclisation of biscarbenoids – a novel mode of cyclobutadiene stabilisation

Author affiliations

Abstract

The reaction of the vicinal biscarbenoid Pip–C[triple bond, length as m-dash]C–Pip with dimethyltin dichloride yields a unique tetraamino-substituted cyclobutadienyl system featuring a dative C–Sn interaction. DFT investigation of the reaction mechanism revealed that coordination of the stannyl fragment to the nucleophilic carbon leads to a metal-stabilised zwitterion, allowing for [2+2] cycloaddition under thermal conditions. The compound features a homoaromatic π-system comprising the three sp2-hybridised carbon atoms of the four-membered ring as a consequence of charge separation.

Graphical abstract: Cyclisation of biscarbenoids – a novel mode of cyclobutadiene stabilisation

Back to tab navigation

Supplementary files

Publication details

The article was received on 23 Sep 2016, accepted on 18 Oct 2016 and first published on 24 Oct 2016


Article type: Communication
DOI: 10.1039/C6CC07741B
Citation: Chem. Commun., 2016,52, 13249-13252

  •   Request permissions

    Cyclisation of biscarbenoids – a novel mode of cyclobutadiene stabilisation

    R. Bertermann, H. Braunschweig, M. A. Celik, T. Dellermann and H. Kelch, Chem. Commun., 2016, 52, 13249
    DOI: 10.1039/C6CC07741B

Search articles by author

Spotlight

Advertisements