Author:
Harrowven David,Sun Wei,Wilson Dharyl
Abstract
Thermally induced rearrangements of 4-hydroxycyclobutenones are known to provide clean and reliable access to an array of useful carbocyclic and fused heterocyclic ring systems. Rarely, such reactions have been diverted to an alternative pathway leading to furanone formation. Herein, we show that these switches in the course of the rearrangement occur when a substrate bears a bulky substituent and are due to adverse steric buttressing as the transition state for electrocyclisation is approached. We also show how the reaction provides new opportunities for furanone synthesis and how bulky proton and halogen surrogates can be used to divert classical rearrangement pathways toward furanone formation. Additionally, we show that classical rearrangement pathways can be promoted by the simple expedient of alcohol protection.
Funder
Engineering and Physical Sciences Research Council
European Regional Development Fund
Subject
Organic Chemistry,Catalysis
Cited by
5 articles.
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