B(C6F5)3 promoted cyclisation of internal propargyl esters: structural characterisation of 1,3-dioxolium compounds

Max M. Hansmann; Rebecca L. Melen; Frank Rominger; A. Stephen K. Hashmi; Douglas W. Stephan

doi:10.1039/C4CC01370K

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B(C₆F₅)₃ promoted cyclisation of internal propargyl esters: structural characterisation of 1,3-dioxolium compounds†

Max M. Hansmann,‡^a Rebecca L. Melen,‡^b Frank Rominger,^a A. Stephen K. Hashmi*^ac and Douglas W. Stephan*^bc

Author affiliations

* Corresponding authors

^a Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
E-mail: hashmi@hashmi.de

^b Department of Chemistry, 80 St. George Street, University of Toronto, Toronto, Ontario, Canada
E-mail: dstephan@chem.utoronto.ca

^c Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), Jeddah 21589, Saudi Arabia

Abstract

The reactions of internal propargyl esters with B(C₆F₅)₃ provide access to stable zwitterionic 1,3-dioxolium compounds which are characterised by X-ray diffraction. These 6π-electron systems show no significant aromatic stabilisation.

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Article information

DOI: https://doi.org/10.1039/C4CC01370K
Article type: Communication
Submitted: 21 Feb 2014
Accepted: 01 May 2014
First published: 12 May 2014

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Chem. Commun., 2014,50, 7243-7245

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B(C₆F₅)₃ promoted cyclisation of internal propargyl esters: structural characterisation of 1,3-dioxolium compounds

M. M. Hansmann, R. L. Melen, F. Rominger, A. S. K. Hashmi and D. W. Stephan, Chem. Commun., 2014, 50, 7243 DOI: 10.1039/C4CC01370K

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