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

Abstract

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.

GRAPHICAL ABSTRACT

Keywords:

• Diazomethane
• hexahydro-1 H-cyclopenta[c]furan-1-one
• norbornane-2,3-dione 3-hemiketal
• oxetane derivative
• rearranged bicyclic product

ACKNOWLEDGMENTS

This work is part of G. H. Mangeswara Rao's Ph.D. thesis, and we thank the Indian Institute of Technology Kanpur (IITK) for Ph.D. registration and for providing the facility to carry out this work.

Notes

Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/lsyc.