Acid-catalyzed intramolecular ring-opening reactions of cyclopropanated oxabenzonorbornadienes with alcohol nucleophiles |
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Authors: | Christopher Wicks Samuel Koh Austin Pounder Emily Carlson William Tam |
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Institution: | Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario N1G 2W1, Canada |
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Abstract: | An investigation of intramolecular ring-opening reactions of various cyclopropanated oxabenzonorbornadienes (CPOBDs) with alcohol nucleophiles is reported, which forms two regioisomeric products in good yields. The effect of various tether lengths was explored, wherein increasing the alcohol tether length to 4 or 5 carbons exclusively generated Type 3 products in good yield, while C-1-hydroxymethyl substituted CPOBD formed a 1,3,5-cycloheptatriene derivative in excellent yield. Electron donating arene and electron withdrawing C-5-bridgehead substituents formed Type 3 major products, whereas electron withdrawing arenes and electron donating C-5 substituents preferentially afforded Type 2 compounds. A mechanism is also proposed for the formation of both regioisomeric products. |
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Keywords: | Corresponding author Acid catalysis Intramolecular Nucleophilic ring-opening Cyclopropanated oxabenzonorbornadiene |
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