217454-83-6

Basic information

• Product Name: 5,17-bis(diphenylphosphonium)-25,26,27,28-tetrapropoxycalix[4]arene
• Synonyms: 5,17-bis(diphenylphosphonium)-25,26,27,28-tetrapropoxycalix[4]arene
• CAS NO: 217454-83-6
• Molecular Weight: 961.173
• Mol File: 217454-83-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 5,17-bis(diphenylphosphonium)-25,26,27,28-tetrapropoxycalix[4]arene(CAS DataBase Reference)
• NIST Chemistry Reference: 5,17-bis(diphenylphosphonium)-25,26,27,28-tetrapropoxycalix[4]arene(217454-83-6)
• EPA Substance Registry System: 5,17-bis(diphenylphosphonium)-25,26,27,28-tetrapropoxycalix[4]arene(217454-83-6)

Safety Data

• Hazardous Substances Data: 217454-83-6(Hazardous Substances Data)

Upstream product

• 1079-66-9 chloro-diphenylphosphine 
• 172472-58-1 5,17-dibromo-25,26,27,28-tetra-n-propylcalix[4]arene 
• 214079-74-0 5,11,17,23-tetrabromo-25,26,27,28-tetrapropoxycalix[4]arene 
• 719-80-2 Ethyl diphenylphosphinite 
• 392743-36-1 5,17-dibromo-26,28-dibenzoyloxy-calix[4]arene 
• 195323-68-3 5,17-dibromo-25,26,27,28-tetrahydroxy-calix[4]arene 
• 176098-88-7 5,17-dibromo-26,28-dihydroxy-25,27-bis(1-propyloxy)calix<4>arene 
• 157544-49-5 25,27-dibenzoyloxy-26,28-dihydroxycalix[4]arene 
• 143406-35-3 25,27-dihydroxy-26,28-dipropoxycalix[4]arene 
• 248590-47-8 25,26,27,28-tetrakis(hydroxy)calix[4]arene 

Downstream Products

• 447460-82-4 cis-P,P'-([5,17-bis(diphenylphosphino)-25,26,27,28-tetrapropoxycalix[4]arene]norbornadiene)rhodium(I) tetrafluoroborate 
• 447460-78-8 dichloro-bis(N,N-dimethylaminobenzylamine)[5,17-bis(diphenylphosphino)-25,26,27,28-tetrapropoxycalix[4]arene]dipalladium(II) 
• 447460-84-6 (η3-2-methylallyl)(P,P'-[5,17-bis(diphenylphosphino)-25,26,27,28-tetrapropoxycalix[4]arene])palladium(II) tetrafluoroborate 
• 448262-64-4 trans-P,P'-dichloro[5,17-bis(diphenylphosphino)-25,26,27,28-tetrapropoxycalix[4]arene]platinum(II) 
• 217192-90-0 [RuCl₂(CO)2((C₆H₃OC₃H₇)CH₂((C₆H₅)2PC₆H₂OC₃H₇)CH₂)2] 
• 217192-87-5 [PdCH₃C₅H₅N((C₆H₃OC₃H₇)CH₂((C₆H₅)2PC₆H₂OC₃H₇)CH₂)2]⁽¹⁺⁾*BF₄^(1-)=[PdCH₃C₅H₅N((C₆H₃OC₃H₇)(CH₂)2((C₆H₅)2PC₆H₂OC₃H₇))2][BF₄] 
• 217192-82-0 [PtHPC₁₈H₁₅((C₆H₃OC₃H₇)CH₂((C₆H₅)2PC₆H₂OC₃H₇)CH₂)2]⁽¹⁺⁾*BF₄^(1-)=[PtHPC₁₈H₁₅((C₆H₃OC₃H₇)CH₂((C₆H₅)2PC₆H₂OC₃H₇)CH₂)2][BF₄] 
• 1093638-37-9 (C₆H₃(OC₃H₇)CH₂C₆H₂(OC₃H₇)(P(C₆H₅)2PtCl(NC₅H₄C₄H₂S))CH₂)2 

Relevant articles and documents

A phosphino calix[4]arene bis-frustrated lewis pair

A bis-frustrated Lewis pair based on a calix[4]arene skeleton is reported for the first time. Importantly, this system has been shown to activate two molecules of hydrogen, thereby establishing a proof of concept for multisite frustrated Lewis pair (FLP) design and synthesis. The complex [calixarene-(Mes2PH+)2][BH(C6F 5)3-]2 (6) has been characterised by X-ray crystal structure analysis. The synthesis and X-ray structure of a calix[4]arene bis-frustrated Lewis pair is described for the first time. This compound is the first example of a frustrated Lewis pair system capable of doubly activating H2 as well as the first use of a calixarene in frustrated Lewis pair chemistry.

Positioning of transition metal centres at the upper rim of cone-shaped calix[4]arenes. Filling the basket with an organometallic ruthenium unit

A series of calix[4]arenes bearing diphenylphosphino groups tethered at the upper rim have been prepared by treatment of 5,11,17,23-tetrabromo-25,26,27,28-tetrapropoxycalix[4]arene with ButLi (or BunLi) followed by reaction with PPh2Cl. The tetraphosphinated derivative 3 was found suitable for the formation of tetranuclear species, notably [3·(AuCl)4], [3·{RuCl2(p-cymene)}4], and [3·{PdCl(o-C6H4CH2NMe2)} 4], all possessing an apparent C4v-symmetry in solution. Reaction of [RuCl2(p-cymene)]2 with the diphosphines 5,17-di-X-11,23-bis(diphenylphosphino)-25,26,27,28-tetrapropoxycalix[4]arene (X = H, 1; X = Br, 4) afforded the C2v-symmetrical dinuclear complexes [1·{RuCl2(p-cymene)}2] and [4·{RuCl2(p-cymene)}2], respectively. Reaction of the non-brominated diphosphine 1 with [PdCl(o-C6H4CH2NMe2)]2 gave the complex [1·{PdCl(o-C6H4CH2NMe2)} 2]. Reaction at high dilution of [PtCl2(1,5-cyclooctadiene)] with 4 or 1 resulted in quantitative formation of the corresponding cis-chelate complexes [4·PtCl2] (12) and [1·PtCl2] (13), respectively. The trans version of 13 could also be obtained, provided that [PtCl2-(PhCN)2] was used as starting complex. In the solid state, the PtCl2 unit of 12 is directed towards one bromine atom, resulting in a highly unsymmetrical calixarene structure where the metal plane is nearly parallel to the calix reference plane. The NMR spectra of 12 and 13 show an apparent C2v-symmetrical structure, suggesting a fast fan-like motion in solution of the metal plane about the P···P axis. Similar dynamics are likely to occur in the related cationic complexes [1·Rh(norbornadiene)]BF4 (15) and [1·Pd(Me-allyl)]BF4 (16). As shown by variable temperature studies carried out on 12 and 16, these dynamics couple with a concomitant, restricted rotation of the two PPh2 units about their coordination axis. The latter motion is probably a result of steric interactions within the phosphorus environment, two PPh rings being in competition for occupation of the cavity entrance. Reaction of the expanded cavity 5,11,17-tribromo-23-diphenylphosphino-25,26,27,28-tetrapropoxycalix[4]arene 5 with [RuCl2(p-cymene)]2 afforded the monophosphine complex [5·RuCl2(p-cymene)]. In solution as well in the solid state, the p-cymene ligand fills the calixarene basket.

Directed positioning of organometallic fragments inside a calix[4]arene cavity

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