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An Expedient Approach to Access Phenalenones via Unconventional [1,2]-Phospha-Brook Rearrangement/Carbonyl Migration
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2024-05-10 , DOI: 10.1021/acs.joc.4c00345
Amjad Ali 1 , Chandana Behera 1 , Ravi P. Singh 1
Affiliation  

An efficient protocol for the synthesis of 2,3-disubstituted phenalenones from para-quinone methides (p-QMs) and acenaphthoquinone is described. The reaction involves P(NMe2)3-mediated [1,2]-phospha-Brook rearrangement followed by Lewis acid-assisted 1,2-carbonyl migration to afford the 2,3-disubstituted phenalenones. The developed protocol tolerates a broad range of substrates to form a variety of phenalenones in good to excellent yields. Moreover, the utility of the synthesized phenalenones is also demonstrated by performing its transformations to other adducts.

中文翻译:


通过非常规 [1,2]-磷酸-布鲁克重排/羰基迁移获取苯烯酮的便捷方法



描述了从对醌甲基化物 (p-QM) 和苊醌合成 2,3-二取代苯烯酮的有效方案。该反应涉及 P(NMe 2 ) 3 介导的 [1,2]-phospha-Brook 重排,然后进行路易斯酸辅助的 1,2-羰基迁移,得到 2, 3-二取代苯那酮。所开发的方案可耐受多种底物,以良好至优异的产率形成各种苯烯酮。此外,通过将其转化为其他加合物,还证明了合成的苯烯酮的实用性。
更新日期:2024-05-10
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