Chemical Communications

Carbenes from vilsmeier reagents by the action of bases in POCl 3; the umpolung of vilsmeier reagents

Y Cheng, S Goon, O Meth-Cohn

Index: Cheng, Ying; Goon, Simon; Meth-Cohn, Otto Chemical Communications, 1996 , # 11 p. 1395 - 1396

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Abstract

When para-substituted N-methylformanilides are treated in POCl3 with a base, the corresponding Vilsmeier reagent formed undergoes ready deprotonation to give an aminochlorocarbene from which a range of products derive; a carba-moyl chloride, N- methylisatins, dimers [1, 2-dichloro-1, 2-bis (N-methyl-N-arylamino) ethenes], trimers {5, 10- dimethyl-11-(N-methyl-N-arylamino)-10H-indolo [3, 2-b] quinolinium and 5, 10-dimethyl- ...