- Base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides
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A novel base-promoted O-deprotonation/alkylation reaction of P(O)-OH compounds with alkyl halides has been developed. The protocol is practical, representing a simple way to produce a broad spectrum of functionalized phosphinates, phosphonates, and phosphates from basic starting materials with good to excellent yields. A plausible mechanism was proposed for this reaction.
- Xiong, Biquan,Ye, Qianqian,Feng, Xiaofeng,Zhu, Longzhi,Chen, Tieqiao,Zhou, Yongbo,Au, Chak-Tong,Yin, Shuang-Feng
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- Some properties of cyclic phosphoramidites and their phosphites: Phosphitylation, ester exchange, and hydrolysis
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Phosphorylation of diols using sterically bulky cyclic phosphoramidites was performed in a good selectivity. Their phosphite derivatives underwent tetrazole-catalyzed hydrolysis and transesterification. The reaction was shown to proceed via a phosphorane intermediate by NMR analysis.
- Watanabe, Yutaka,Maehara, Shin-Ich
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p. 799 - 810
(2007/10/03)
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- 1H-Tetrazole Catalysed Reactions of Trialkyl Phosphites: Observation of a Five-membered Cyclic Hydrophosphorane Intermediate during the Transesterification
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1H-Tetrazole-catalysed transesterification of a trialkyl phosphite with an alcohol and a (31)P NMR experiment in the case of 4,4,5,5-tetramethyl-2-(3-phenylpropoxy)-1,3,2-dioxaphospholane showed the existence of the corresponding cyclic five-coordinate hydrophosphorane as an intermediate.
- Watanabe, Yutaka,Maehara, Shin-ichi,Ozaki, Shoichiro
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p. 1879 - 1880
(2007/10/02)
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