Abstract
para-Quinones feature extensively as targets and/or intermediates throughout a number
of chemical and biological subdisciplines, highlighting the importance of efficient
preparative methods. This Synpacts article provides an overview of ring forming approaches
to para-hydroquinones and para-benzoquinones, concluding with our recent contribution concerning the development
of 2,5-bis(tert-butyldimethylsilyloxy)furans as vicinal bisketene equivalents in the Diels–Alder
reaction.
1 Introduction
2 Ring Forming Approaches to para-Quinones
2.1 Hauser–Kraus Annulation
2.2 Moore–Liebeskind Rearrangement
2.3 Wulff–Dötz Reaction
2.4 Oxidative Bergman Cyclization
2.5 Diels–Alder Strategies
2.5.1 Ketene–Enol Equivalents
2.5.2 Bisketene Equivalents
3 Toward an Improved Bisketene Equivalent
4 Conclusion
Key words
Diels–Alder - cycloaddition - annulation - hydroquinone - benzoquinone - furan
