The Journal of organic chemistry

Photoactivation of amino-substituted 1, 4-benzoquinones for release of carboxylate and phenolate leaving groups using visible light

Y Chen, MG Steinmetz

文献索引：Chen, Yugang; Steinmetz, Mark G. Journal of Organic Chemistry, 2006 , vol. 71, # 16 p. 6053 - 6060

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被引用次数: 37

摘要

Upon exposure to visible light, 2-pyrrolidino-substituted 3, 6-dimethyl-1, 4-benzoquinones photocyclize to give benzoxazolines with quantum yields of 0.07-0.10 in CH2Cl2, 0.02-0.04 in CH3CN, and< 0.01 in 30% aq CH3CN. With carboxylate or phenolate leaving groups incorporated via coupling to a 5-hydroxymethyl group of the quinones, the photocyclizations give benzoxazolines that eliminate the leaving groups in a dark reaction. Lifetimes for ...