EventsThe 3rd International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-3-01728
This submission belongs to the session a. General Organic Synthesis of the event The 3rd International Electronic Conference on Synthetic Organic Chemistry
Published date
01 Nov, 1999
Citation
Edward R. T. Tiekink, Shudong Wang, Douglas N. Butler, Ronald N. Warrener, 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., in Proceedings of The 3rd International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 1999, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-3-01728
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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.

Ronald N. Warrener 1
Douglas N. Butler 1
Shudong Wang 1
Edward R. T. Tiekink 1
1. Director, Centre for Molecular Architecture, Central Queensland University, Bruce Highway, ROCKHAMPTON QLD 4702
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
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