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 Warrener; Douglas Butler; Shudong Wang; Edward Tiekink

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

^*,

Douglas N. Butler

Shudong Wang

Edward R. T. Tiekink

¹ Director, Centre for Molecular Architecture, Central Queensland University, Bruce Highway, ROCKHAMPTON QLD 4702

Published: 01 November 1999 by MDPI in The 3rd International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-3-01728

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.

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Ronald Warrener

Douglas Butler

Shudong Wang

Edward Tiekink