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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/667

Title: Synthetic and theoretical investigations on the construction of oxanorbornenes by a Michael addition and intramolecular Diels-Alder furan reaction
Authors: DADWAL, MAMTA
KESHARWANI, MANOJ K
DANAYAK, VAISHALEE
GANGULY, BISHWAJIT
SHAIKH, MOBIN M
MURUGANANTHAM, RAJENDRAN
NAMBOOTHIRI, IRISHI NN
Keywords: intramolecular
isomer
ab initio calculations
Issue Date: 2008
Publisher: WILEY-VCH Verlag GmbH & Co. KGaA
Citation: European Journal of Organic Chemistry 2008(36), 6106-6118
Abstract: The conjugate addition of nucleophiles such as allylmercaptan,allyl- and homoallylmalonate and diallylamine to ß-furyl enones and acrylate, provides the Michael adducts in good yield. A facile intramolecular Diels-Alder reaction between the unsaturated tether and the furan diene ensues when these adducts are heated in a solvent such as toluene or xylene to afford the cycloadducts in good yield and excellent stereoselectivity in most cases. The structure and stereo-chemistry of these cycloadducts were confirmed by extensive NMR experiments and X-ray crystallography. Quantum chemical calculations on the transition state and product geometries suggest that the formation of the cycloadducts, in which the newly formed ring is exo-fused to the oxanorbornene framework, is favored over the endo-fused product due to less strain in the former and its transition state.
URI: http://dx.doi.org/10.1002/ejoc.200800681
http://hdl.handle.net/10054/667
http://dspace.library.iitb.ac.in/xmlui/handle/10054/667
ISSN: 1099-0690
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