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; S. J. Williams

doi:10.1039/b104110j

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, S. J. Williams

^*Corresponding author for this work

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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.

Original language	English
Pages (from-to)	1586-1593
Number of pages	8
Journal	Journal of the Chemical Society. Perkin Transactions 1
Issue number	14
DOIs	https://doi.org/10.1039/b104110j
Publication status	Published - 2001

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title = "Preparation of tetraalkylformamidinium salts and related species as precursors to stable carbenes",

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.",

author = "Alder, \{R. W.\} and Blake, \{M. E.\} and S. Bufali and Butts, \{C. P.\} and Orpen, \{A. G.\} and J. Sch{\"u}tz and Williams, \{S. J.\}",

year = "2001",

doi = "10.1039/b104110j",

language = "English",

pages = "1586--1593",

journal = "Journal of the Chemical Society. Perkin Transactions 1",

issn = "1472-7781",

publisher = "Chemical Society",

number = "14",

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TY - JOUR

T1 - Preparation of tetraalkylformamidinium salts and related species as precursors to stable carbenes

AU - Alder, R. W.

AU - Blake, M. E.

AU - Bufali, S.

AU - Butts, C. P.

AU - Orpen, A. G.

AU - Schütz, J.

AU - Williams, S. J.

PY - 2001

Y1 - 2001

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0034742920

U2 - 10.1039/b104110j

DO - 10.1039/b104110j

M3 - Article (Academic Journal)

AN - SCOPUS:0034742920

SN - 1472-7781

SP - 1586

EP - 1593

JO - Journal of the Chemical Society. Perkin Transactions 1

JF - Journal of the Chemical Society. Perkin Transactions 1

IS - 14

ER -

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

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