2015
DOI: 10.1002/ejoc.201500772
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Tetrasulfonated 1,2‐Bis(diphenylphosphanyl)ethane as a Building Block for the Synthesis of Disulfonated Alkyldiphenylphosphanes

Abstract: International audienceno abstrac

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Cited by 2 publications
(4 citation statements)
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“…The global yields of these two steps (alkylation and cleavage) were 60 %, 54 %, and 51 % for disulfonated alkyldiphenylphosphanes 1, 2 and 3, respectively. Table 1 gathers the yields obtained for the synthesis of these three sulfonated phosphanes both in our previous work (DPPETS pathway) [8] and in this publication (BDPPTS pathway). The global yields obtained for the alkylation and cleavage steps are always higher for the BDPPTS pathway (factor 1.3, 1.2, and 1.3 for phosphanes 1, 2, and 3, respectively).…”
Section: Resultsmentioning
confidence: 95%
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“…The global yields of these two steps (alkylation and cleavage) were 60 %, 54 %, and 51 % for disulfonated alkyldiphenylphosphanes 1, 2 and 3, respectively. Table 1 gathers the yields obtained for the synthesis of these three sulfonated phosphanes both in our previous work (DPPETS pathway) [8] and in this publication (BDPPTS pathway). The global yields obtained for the alkylation and cleavage steps are always higher for the BDPPTS pathway (factor 1.3, 1.2, and 1.3 for phosphanes 1, 2, and 3, respectively).…”
Section: Resultsmentioning
confidence: 95%
“…Thus, we recently described a new pathway from tetrasulfonated 1,2‐bis(diphenylphosphanyl)ethane (DPPETS) and an alkyl bromide. DPPETS was alkylated and then cleaved to produce the targeted phosphanes (Scheme a) . This strategy used the property of the quaternary bis(phosphonium) salts of DPPETS to be cleaved by lithium aluminium hydride (LiAlH 4 ) producing a disulfonated alkyldiphenylphosphane with loss of ethylene and H 2 .…”
Section: Introductionmentioning
confidence: 99%
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“…As already mentioned in the introduction to this chapter, the harsh reaction conditions usually associated with direct sulfonation are not compatible with all structural features of common phosphine ligands. Examples for oleum‐sensitive groups on alkyldiphenylphosphines are long alkyl chains (>C 6 ) or alkenyl substituents [35] . While alkyl chains longer than hexyl are cleaved, [36] the double bond of an alkenyl moiety would be protonated and thus susceptible to side reactions [35] …”
Section: Current Strategies Towards Water‐soluble Phosphorus Ligandsmentioning
confidence: 99%