Photoreactivity of 2-pyridones with furan, benzene, and naphthalene. Inter- and intramolecular photocycloadditions.
Photoreactivity of 2-pyridones with furan, benzene, and naphthalene. Inter- and intramolecular photocycloadditions.
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2-吡啶酮与呋喃、苯和萘的光反应性。
DOI：
10.1021/jo9918394
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发表时间：
2000
期刊：
影响因子：
--
通讯作者：
Chen,Y
中科院分区：
文献类型：
--
作者：
Sieburth,SM;McGeeJr,KF;Zhang,F;Chen,Y
吡啶酮具有光二聚化的能力，已被发现与呋喃和萘发生[4 + 4]光环加成反应，但与苯不发生[4 + 4]光环加成反应。在某些情况下，这些反应可以是高度区域特异性和立体特异性的。与呋喃的分子内反应产生顺式和反式[4 + 4]产物。与萘的环加成可以在分子间和分子内发生。分子间反应主要产生顺式异构体，而反式异构体是分子内反应的主要产物。4-甲氧基-2-吡啶酮和2-甲氧基萘的混合物可形成多达8种区域和立体异构体，主要形成一种[4 + 4]产物。
Pyridones, well-known for their ability to photodimerize, have been found to undergo [4 + 4] photocycloaddition with furan and naphthalene but not with benzene. In some cases these reactions can be highly regio- and stereospecific. Intramolecular reaction with furan produces both cis and trans [4 + 4] products. The cycloaddition with naphthalene can occur both inter- and intramolecularly. The intermolecular reaction yields primarily the cis isomer, whereas the trans isomer is the major product from the intramolecular reaction. A mixture of 4-methoxy-2-pyridone and 2-methoxynaphthalene that could form up to eight regio- and stereoisomers forms largely one [4 + 4] product.