Tetrahedron

Diels-Alder reaction of 4-bromo-6-spiroepoxycyclohexa-2, 4-dienone with electron-rich and neutral dienophiles

V Bonnarme, C Bachmann, A Cousson, M Mondon…

文献索引：Bonnarme, Vincent; Bachmann, Christian; Cousson, Alain; Mondon, Martine; Gesson, Jean-Pierre Tetrahedron, 1999 , vol. 55, # 2 p. 433 - 448

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被引用次数: 25

摘要

Spirodienone 1, prepared by Adler-Becker oxidation of 4-bromo-2-hydroxymethylphenol, undergoes [4+ 2] cycloaddition with various dienophiles (enol ethers, enol esters, styrenes, N-methylvinylacetamide) under thermal conditions (20–160° C). Three sets of experiments have been carried out, either with CH2Cl2 as solvent or neat with 1, or under tandem oxidation-cycloaddition conditions with phase-transfer catalysis. Complete regio-and syn ...