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- W2312562110 endingPage "1385" @default.
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- W2312562110 abstract "The addition of P(O)–H bonds to internal alkenes has been accomplished under solvent-free conditions without the addition of a catalyst or radical initiator. Using a prototypical secondary phosphine oxide, a range of substrates including cinnamates, crotonates, coumarins, sulfones, and chalcones were successfully functionalized. Highly activated acceptors such as isopropylidenemalononitrile and ethyl 2-cyano-3-methyl-2-butenoate underwent the phospha-Michael reaction upon simple trituration of the reagents at room temperature, whereas less activated substrates such as ethyl cinnamate and methyl crotonate required heating (>150 °C) in a microwave reactor to achieve significant consumption of the starting alkenes. For the latter alkenes, a competing reaction involving disproportionation of the ditolylphosphine oxide into ditolylphosphinic acid and ditolylphosphine was observed at the high temperatures needed to promote the addition reaction." @default.
- W2312562110 created "2016-06-24" @default.
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- W2312562110 date "2012-01-13" @default.
- W2312562110 modified "2023-10-04" @default.
- W2312562110 title "Phospha-Michael Additions to Activated Internal Alkenes: Steric and Electronic Effects" @default.
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- W2312562110 doi "https://doi.org/10.1021/jo202183u" @default.
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