Permanent URL to this publication: http://dx.doi.org/10.5167/uzh-50021
Nikolaev, V V; Linden, A; Heimgartner, H (2007). Thermolysis of imidates: A new method for the generation of carbonyl ylides. Helvetica Chimica Acta, 90(12):2330-2341.
PDF - Registered users only
View at publisher
Thermolysis of dimethyl 2-[(3-oxo-3H-isoindol-1-yl)oxy]malonate (8) promotes a [1,4]-H shift in the imidic N¼C O CH fragment of the starting molecule, which leads to a reactive carbonyl ylide. This carbonyl ylide can be trapped by the C¼N bond of imidates and imines, as well as the C¼O bond of benzaldehyde. The corresponding cycloadducts 11, 14, and 16 are formed regioselectively in good yields (60 – 95%) and with high stereoselectivity. In the case of 11, the minor cycloadduct in solution undergoes an isomerization to give the more stable stereoisomer. The structures of two cycloadducts, i.e., 11a and 14a, have been established by X-ray crystallography.
54 downloads since deposited on 20 Oct 2011
15 downloads since 12 months
|Item Type:||Journal Article, refereed, original work|
|Communities & Collections:||07 Faculty of Science > Department of Chemistry|
|Dewey Decimal Classification:||540 Chemistry|
|Deposited On:||20 Oct 2011 12:09|
|Last Modified:||19 Jun 2014 17:10|
|Publisher:||Verlag Helvetica Chimica Acta|
|Funders:||F. Hoffmann-La Roche AG, Basel|
Users (please log in): suggest update or correction for this item
Repository Staff Only: item control page