Preparation of tetraalkylformamidinium salts and related species as precursors to stable carbenes

Roger W. Alder; Michael E. Blake; Simone Bufali; Craig P. Butts; A. Guy Orpen; Jan Schütz; Stuart J. Williams

doi:10.1039/B104110J

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Preparation of tetraalkylformamidinium salts and related species as precursors to stable carbenes

Roger W. Alder,*^a Michael E. Blake,^a Simone Bufali,^a Craig P. Butts,*^b A. Guy Orpen,^a Jan Schütz^a and Stuart J. Williams^a

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^a School of Chemistry, University of Bristol, Cantock's Close, Bristol, UK

^b School of Chemistry, University of Exeter, Stocker Rd, Exeter, UK

Abstract

Methods are described for the preparation of a range of N,N,N′,N′-tetraalkylformamidinium and N,N-dialkyliminium ions 4–20 as anhydrous salts for use as precursors to diamino- and amino-carbenes. These methods include a novel method involving nucleophilic addition to formamides followed by trapping with electrophiles such as triflic anhydride, various methods of formamide activation, exchange reactions involving orthoesters and the transamination of amidinium salts, and alkylation methods.

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Article information

DOI: https://doi.org/10.1039/B104110J
Article type: Paper
Submitted: 04 May 2001
Accepted: 07 Jun 2001
First published: 27 Jun 2001

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J. Chem. Soc., Perkin Trans. 1, 2001, 1586-1593

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Preparation of tetraalkylformamidinium salts and related species as precursors to stable carbenes

R. W. Alder, M. E. Blake, S. Bufali, C. P. Butts, A. G. Orpen, J. Schütz and S. J. Williams, J. Chem. Soc., Perkin Trans. 1, 2001, 1586 DOI: 10.1039/B104110J

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Journal of the Chemical Society, Perkin Transactions 1

Preparation of tetraalkylformamidinium salts and related species as precursors to stable carbenes

Abstract

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Preparation of tetraalkylformamidinium salts and related species as precursors to stable carbenes

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