Khan, Faiz Ahmed ; Satapathy, Rashmirekha ; Sudheer, Ch. ; Nageswara Rao, Ch. (2005) A new reaction of diazomethane with norbornyl α-diketones Tetrahedron Letters, 46 (42). pp. 7193-7196. ISSN 0040-4039
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2005.08.087
Abstract
A new reaction of diazomethane with norbornyl α-diketones in MeOH as solvent leading regioselectively to ketals is described. The mechanistic details of this intriguing reaction were investigated employing d4-MeOH, EtOH and d6-EtOH. The surprising observation of complete deuterium incorporation in the diazomethane-derived methoxy group was accounted for by sequential deuterium exchange between the initially formed hemiketal d4-18 and diazomethane in the presence of d4-MeOH as solvent.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Diazomethane; α-Diketones; Ketal; Regioselectivity; Oxiranes |
| ID Code: | 80328 |
| Deposited On: | 31 Jan 2012 14:27 |
| Last Modified: | 31 Jan 2012 14:27 |
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