Tetrahedron letters

3-bromo-2-pyrone: an easily prepared chameleon diene and a synthetic equivalent of 2-pyrone in thermal diels-alder cycloadditions

GH Posner, TD Nelson, CM Kinter, K Afarinkia

文献索引：Posner, Gary H.; Nelson, Todd D.; Kinter, Chris M.; Afarinkia, Kamyar Tetrahedron Letters, 1991 , vol. 32, # 39 p. 5295 - 5298

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被引用次数: 52

摘要

Abstract 3-Bromo-2-pyrone, a stable solid prepared by a new route (eq. 1), has been found to undergo smooth and regiospecific 2+ 4-cycloadditions between 78-90 C with both electron-rich and electron-deficient dienophiles; subsequent high-yield reductive debrominations produced halogen-free cycloadducts thus showing 3-bromo-2-pyrone to be a practical and effective synthetic equivalent of 2-pyrone in thermal Diels-Alder ...