Reactions of Dimethoxycarbene with N‐Tosylated Imines |
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| Authors: | Grzegorz Mlostoń John Warkentin Anthony Linden Heinz Heimgartner |
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| Affiliation: | 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. Department of Chemistry, McMaster University, 1280 Main Street West, Hamilton, Ontario L8S 4M1, Canada;4. Organisch‐chemisches Institut der Universit?t Zürich, Winterthurerstrasse 190, CH‐8057 Zürich, (phone: +41?44?635?4282;5. fax: +41?44?635?6812) |
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| 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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| Keywords: | Azomethine ylides Aziridines Carbenes Imines Rearrangements |
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