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Updated: Jul 31, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Diversity in the Synthesis of Functionalized Cyclohexene Oxide Derivatives by a Cycloaddition-Fragmentation Sequence
Flavie Rambaud1, Régis Guillot1, Valérie Alezra1
1Institut de Chimie Moléculaire et des Matériaux d'Orsay, CNRS, Université de Paris-Saclay, Bâtiment Henri Moissan, F-91405 Orsay, France.
Abstract:
A cycloaddition-fragmentation sequence from benzene oxide and a nitroso- or azo-dienophile was investigated as a tool for access to highly substituted cyclohexene oxide derivatives. Alkyl lithium-promoted fragmentation of the cycloadducts led to the cyclic derivatives after 1,4- or 1,2-addition of a second equivalent of the lithium reagent. New fragmentation processes were observed when using non-nucleophilic bases of highly hindered alkyl lithium reagents. All reactions proceeded with complete stereocontrol.
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