1983
DOI: 10.1021/om50001a027
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Synthesis and reactivity of some p-mesityl-substituted phosphorus compounds

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Cited by 16 publications
(3 citation statements)
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“…Thus with (MesCu) x and excess PCl 3 , MesPCl 2 can be produced in 95% yield based on the organocopper reagent (NMR evidence). According to Xie and Neilson, MesPCl 2 can also be produced on a large scale by the reaction of MesMgBr with PCl 3 , but no details of the procedure are given [23]. In our experience, the reaction of DippMgBr with PCl 3 in many trials leads exclusively to a mixture of all three halides, DippPBr 2 , DippPBrCl and DippPCl 2 in distributions that imply that all the bromide originally introduced from the Grignard reagent ends up on phosphorus, a remarkable testimony to the greater nucleophilicity of bromide relative to chloride ( 31 P NMR and mass spectroscopic evidence) [19].…”
Section: Synthesis Of (Dippcu) X and Dipppclmentioning
confidence: 99%
“…Thus with (MesCu) x and excess PCl 3 , MesPCl 2 can be produced in 95% yield based on the organocopper reagent (NMR evidence). According to Xie and Neilson, MesPCl 2 can also be produced on a large scale by the reaction of MesMgBr with PCl 3 , but no details of the procedure are given [23]. In our experience, the reaction of DippMgBr with PCl 3 in many trials leads exclusively to a mixture of all three halides, DippPBr 2 , DippPBrCl and DippPCl 2 in distributions that imply that all the bromide originally introduced from the Grignard reagent ends up on phosphorus, a remarkable testimony to the greater nucleophilicity of bromide relative to chloride ( 31 P NMR and mass spectroscopic evidence) [19].…”
Section: Synthesis Of (Dippcu) X and Dipppclmentioning
confidence: 99%
“…Surprisingly, reaction of 1 with one equiv PCl 3 did not proceed with similar chemoselectively and gave substantial amounts of Mes 2 PCl ( 7 ; 40%) in addition to MesPCl 2 ( 6 ; 60%) (Scheme ). However, when an excess of PCl 3 was used (2 equiv), 6 was formed almost exclusively and was isolated in 82% yield after distillation 2 Reaction of 1 with MCl 3 (M = B, P) and 1,1‘-fc(BBr 2 ) 2 …”
Section: Resultsmentioning
confidence: 99%
“…95% yield according to 1 H NMR spectroscopy of the crude product. Distillation under reduced pressure gave spectroscopically pure 6 (0.90 g, 82%) …”
Section: Methodsmentioning
confidence: 99%