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Site and Stereoselectivities in the High Pressure Reactionof Furan with Dimethyl 7-isopropylidenebicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate and Tetramethyl7-isopropylidenebicyclo[2.2.1]hepta-2,5-diene-2,3,5,6-tetracarboxylate.
Published:
01 November 1999
by MDPI
in The 3rd International Electronic Conference on Synthetic Organic Chemistry
session General Organic Synthesis
Abstract: Furan 16 is shown to react under high pressure (14 kbar) with dimethyl 7-isopropylidene norbornadiene-2,3-dicarboxylate 4 to form two 1:1-adducts 17 and 19 (only 17 isolated) by exclusive reaction at the ester-substituted p -bond and 2:1-products 18 and 20 (X-ray analysis) by further in situ cycloaddition of furan 16 at the newly formed 7-oxa norbornene p-bond of the 1:1-adducts. Similar 1:1-adducts 26, 27 and 2:1-adducts 28, 29 were obtained in the high pressure addition of furan 16 with tetramethyl 7-isopropyl idenenorbornadiene-2,3,5,6-tetracarboxylate 5.
Keywords: n/a
