Ozonization: An Efficient Method for the Oxidation of Halophosphines

Caminade, Anne‐Marie; Khatib, F. El; Baceiredo, Antoine; Koenig, Max

doi:10.1080/03086648708080523

Cited by 9 publications

(2 citation statements)

References 6 publications

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“…Cyclic products may be obtained from 13 either by a double-oxidative Hay coupling reaction ("shot-gun" approach) or in a stepwise manner. The latter requires monosilylation (14), coupling, deprotection, and cyclization steps. However, treatment of 13 with EtMgBr or n-BuLi at -78°C Ǟ -30°C followed by Et 3 SiCl quenching gave 14 in only 13 % yield as a moderately stable pale-white solid [δ( 31 P) = -23.2 ppm (Si-CϵC-P), -22.2 ppm (HCϵC-P)], which makes the stepwise route impractical for the synthesis of macrocycles.…”

Section: Grignard Reactionsmentioning

confidence: 99%

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Acetylene‐Substituted Phosphane Oxides: Building Blocks for Macrocycles

et al. 2007

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Phosphorus-based macrocycles with acetylenic scaffolds have been built from acetylene-substituted phosphane oxides that were formed from diisopropylphosphoramidic dibromide (3) and an acetylenic Grignard reagent. The fourand six-edged macrocycles 15 and 16, in which the iPr 2 NP(O) units are connected through 1,3-butadiyne rods, were obtained from the monosilylated derivative of iPr 2 NP(O)(C 2 H) 2 (7) by multiple acetylene coupling reactions under oxidative

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Section: Grignard Reactionsmentioning

confidence: 99%

“…[13] enabling further substitution. Instead of dibromide 3 we also explored the potential of iPr 2 NP(O)Cl 2 , synthesized from iPr 2 NPCl 2 by ozone oxidation, [14] as a precursor to 6, but reaction with BrMgCϵCTMS (4) required temperatures above 50°C, causing degradation of the Grignard reagent.…”

Section: Introductionmentioning

confidence: 99%