Umpoled Vilsmeier reagents. The chemistry of aminochlorocarbenes derived from Vilsmeier reagents by the action of bases1
Y Cheng, S Goon, O Meth-Cohn
Index: Cheng, Ying; Goon, Simon; Meth-Cohn, Otto Journal of the Chemical Society - Perkin Transactions 1, 1998 , # 10 p. 1619 - 1625
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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 (ie 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 ...
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