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Reactions of Dimethoxycarbene with N-Tosylated Imines

✍ Scribed by Grzegorz Mlostoń; John Warkentin; Anthony Linden; Heinz Heimgartner

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

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✦ Synopsis

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 different adducts with rearranged skeletons. In the case of 3a, the 1 : 1 adduct 5 as well as the 2 : 1 adduct 6 were obtained (Scheme 2). The formation of both products can be explained by a migration of a MeO group of the DMC fragment in a zwitterionic intermediate. On the other hand, migration of a Me group of DMC is necessary for the formation of the two 1 : 1 adducts 13 and 14 of 2 and 3d (Scheme 5). The structures of all products have been established by X‐ray crystallography.

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