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The First Reaction of Dimethoxycarbene with an Imine Moiety
Author(s) -
Mlostoń Grzegorz,
Heimgartner Heinz
Publication year - 2007
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200790185
Subject(s) - chemistry , nucleophile , aldimine , imine , moiety , derivative (finance) , sulfonyl , medicinal chemistry , toluene , yield (engineering) , thermal decomposition , bond cleavage , organic chemistry , combinatorial chemistry , catalysis , alkyl , materials science , financial economics , economics , metallurgy
The nucleophilic dimethoxycarbene (DMC; 2 ) generated by thermal decomposition of 2,5‐dihydro‐1,3,4‐oxadiazole derivative 1 in boiling toluene reacts smoothly with N ‐(9 H ‐fluoren‐9‐ylidene)‐4‐methylbenzenesulfonamide ( 7b ) to yield carbonimidoate derivative 10 . A multi‐step reaction pathway, initiated by the attack of DMC onto the CN bond and followed by the migration of the sulfonyl group (or via a sulfinate anion) is proposed to explain the formation of the final product. In contrast to the formal ketimine 7b , N ‐benzylidene‐4‐methylbenzenesulfonamide ( 7a ), a formal aldimine, does not react with DMC under comparable conditions.