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Reactions of dimethoxycarbene with N-tosylated imines


Mloston, G; Warkentin, J; Linden, A; Heimgartner, H (2007). Reactions of dimethoxycarbene with N-tosylated imines. Helvetica Chimica Acta, 90(10):2024-2036.

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.

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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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2007
Deposited On:20 Oct 2011 12:31
Last Modified:05 Apr 2016 15:02
Publisher:Verlag Helvetica Chimica Acta
ISSN:0018-019X
Funders:Polish Ministry of Education and Science (grant No. PBZ-KBN-126/T09/12), F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/hlca.200790210

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