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DOI: 10.1039/A800800K (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 1619-1626

Umpoled Vilsmeier reagents. The chemistry of aminochlorocarbenes derived from Vilsmeier reagents by the action of bases[hair space]1

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Ying Cheng, Simon Goon and Otto Meth-Cohn

Abstract

Vilsmeier reagents such as N-methyl-N-phenylchloroiminium chloride are readily deprotonated by tert-amines even in POCl3 solution. The resulting transient intermediates, aminochlorocarbenes, are nucleophilic (i.e. umpoled Vilsmeier reagents) and are trapped with electrophiles. In this way dimers [1,2-bis(N-methylanilino)-1,2-dichloroethanes] 3, ‘trimers’ (indolo[3,2-b]quinolininium chlorides) 4 and 5, ‘tetramers’ (2,2′-bis-indoles) 11 and isatins 9 and 10 are accessible in one-pot processes from the formanilide.

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