The First Reaction of Dimethoxycarbene with an Imine Moiety |
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| Authors: | Grzegorz Mlostoń Heinz Heimgartner |
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| Institution: | 1. University of ?ód?, Department of Organic and Applied Chemistry, Narutowicza 68, PL‐90‐136 ?ód?, (phone: +48?42?635?5761;2. fax: +48?42?635?5380);3. Organisch‐chemisches Institut der Universit?t Zürich, Winterthurerstrasse 190, CH‐8057 Zürich, (phone: +41?44?635?4282;4. fax: +41?44?635?6812) |
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| Abstract: | 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 C?N 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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| Keywords: | Azomethine ylides Aziridines Carbenes Imines Carbonimidoates Ylides |
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