A Solvent Effect in the Reaction of Diazomethane with Norbornane-2,3-dione 3-Hemiketals

Rao, G H M and Khan, Faiz Ahmed (2014) A Solvent Effect in the Reaction of Diazomethane with Norbornane-2,3-dione 3-Hemiketals. Synthetic Communications, 44 (22). pp. 3314-3319. ISSN 0039-7911

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A solvent effect in the reaction of diazomethane with norbornane-2,3-dione 3-hemiketal in various aprotic solvents such as ether, dichloromethane, tetrahydrofuran (THF), dioxane, and chloroform is reported. Unlike in methanol, preparatively useful quantities of oxetane derivatives were obtained along with a novel hexahydro-1H-cyclopenta[c]furan-1-one in these aprotic solvents. Dichloromethane and THF gave optimal yields of the two products. In some cases, α-ketoketals were formed as minor products along with the aforementioned products. Interestingly, TMSCHN2 furnished hexahydro-1H-cyclopenta[c]furan-1-one as the predominant product.

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IITH Creators:
IITH CreatorsORCiD
Item Type: Article
Uncontrolled Keywords: Diazomethane,hexahydro-1 H-cyclopenta[c]furan-1-one,norbornane-2,3-dione 3-hemiketal, oxetane derivative,rearranged bicyclic product
Subjects: ?? sub5.8 ??
Divisions: Department of Chemistry
Depositing User: Library Staff
Date Deposited: 05 Mar 2015 11:11
Last Modified: 21 Sep 2017 06:50
URI: http://raiith.iith.ac.in/id/eprint/1375
Publisher URL: https://doi.org/10.1080/00397911.2014.926554
OA policy: http://www.sherpa.ac.uk/romeo/issn/0039-7911/
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