The First Reaction of Dimethoxycarbene with an Imine Moiety
Grzegorz Mlostoń
University of Łódź, Department of Organic and Applied Chemistry, Narutowicza 68, PL-90-136 Łódź, (phone: +48 42 635 5761; fax: +48 42 635 5380)
Search for more papers by this authorHeinz Heimgartner
Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, (phone: +41 44 635 4282; fax: +41 44 635 6812)
Search for more papers by this authorGrzegorz Mlostoń
University of Łódź, Department of Organic and Applied Chemistry, Narutowicza 68, PL-90-136 Łódź, (phone: +48 42 635 5761; fax: +48 42 635 5380)
Search for more papers by this authorHeinz Heimgartner
Organisch-chemisches Institut der Universität Zürich, Winterthurerstrasse 190, CH-8057 Zürich, (phone: +41 44 635 4282; fax: +41 44 635 6812)
Search for more papers by this authorAbstract
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-(9H-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.
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