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The First Reaction of Dimethoxycarbene with an Imine Moiety

✍ Scribed by Grzegorz Mlostoń; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
2007
Tongue
German
Weight
98 KB
Volume
90
Category
Article
ISSN
0018-019X

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✦ Synopsis

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‐(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 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.

📜 SIMILAR VOLUMES

Reactions of Dimethoxycarbene with N-Tos
Reactions of Dimethoxycarbene with N-Tosylated Imines
✍ Grzegorz Mlostoń; John Warkentin; Anthony Linden; Heinz Heimgartner 📂 Article 📅 2007 🏛 John Wiley and Sons 🌐 German ⚖ 308 KB 👁 2 views

## Abstract The reactions of dimethoxycarbene (DMC; **2**), which was generated __in situ__ by thermal decomposition of 2,5‐dihydro‐2,2‐dimethoxy‐5,5‐dimethyl‐1,3,4‐oxadiazole (**1**), with __N__‐tosylated imines of xanthone and 2,3 : 6,7‐dibenzosuberenone, **3a** and **3d**, respectively, led to d