Abstract
The syntheses, structural properties, and reactivities are reviewed for phosphine-acetylenic macrocycles and cages. These compounds are of current interest for their phosphorus-containing π-conjugated molecular frameworks. A distinction is made between organic compounds, in which the building blocks are assembled by consecutive transformations, and organometallic structures, in which the coordinative ability of phosphorus is employed to assemble the monomeric building blocks.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Baumgartner T, Réau R (2006) Organophosphorus π-conjugated materials. Chem Rev 106:4681–4727
Hissler M, Dyer PW et al (2005) The rise of organophosphorus derivatives in π-conjugated materials chemistry. Top Curr Chem 250:127–163
Hissler M, Lescop C et al (2005) Organophosphorus π-conjugated materials: the rise of a new field. J Organomet Chem 690:2482–2487
Hissler M, Dyer PW et al (2003) Linear organic π-conjugated systems featuring the heavy group 14 and 15 elements. Coord Chem Rev 244:1–44
Hightower SE, Corcoran RC et al (2005) Unusual, bifurcated photoreactivity of a rhenium(I) carbonyl complex of triethynylphosphine. Inorg Chem 44:9601–9603
Ochida A, Ito H et al (2006) Using triethynylphosphine ligands bearing bulky end caps to create a holey catalytic environment: application to gold(I)-catalyzed alkyne cyclizations. J Am Chem Soc 128:16486–16487
Ochida A, Sawamura M (2007) Phosphorus ligands with a large cavity: synthesis of triethynylphosphines with bulky end caps and application to the rhodium-catalyzed hydrosilylation of ketones. Chem Asian J 2:609–618
Kondoh A, Yorimitsu H et al (2007) Synthesis of bulky phosphines by rhodium-catalyzed formal [2 + 2 + 2] cycloaddition reactions of tethered diynes with 1-alkynylphosphine sulfides. J Am Chem Soc 129:6996–6997
Van Assema SGA, Tazelaar CGJ et al (2008) Phospha-scorpionate complexes by click chemistry using phenyl azide and ethynylphosphine oxides. Organometallics 27:3210–3215
Lammertsma K (2003) Phosphinidenes. Top Curr Chem 229:95–119
Mathey F (1988) The organic chemistry of phospholes. Chem Rev 88:429–453
Huy NHT, Perrier E et al (2006) The use of phosphirenes as conjugating spacers in polythiophene chains. Organometallics 25:5176–5179
Huy NHT, Ricard L et al (2001) Stepwise building of polyphosphirene chains. Angew Chem Int Ed 40:1253–1255
Marinetti A, Mathey F et al (1982) Generation and trapping of terminal phosphinidene complexes. Synthesis and X-ray crystal structure of stable phosphirene complexes. J Am Chem Soc 104:4484–4485
Borst MLG, Bulo RE et al (2005) 3H-Benzophosphepine complexes: versatile phosphinidene precursors. J Am Chem Soc 127:16985–16999
Regitz M, Hoffman A et al (1995) Phosphaalkynes—starting point for the synthesis of phosphorus-carbon cage compounds. In: Stang PJ, Diederich F (eds) Modern acetylene chemistry, 1st edn. VCH, Weinheim
Regitz M (1990) Phosphaalkynes: new building blocks in synthetic chemistry. Chem Rev 90:191–213
Regitz M (1994) Organophosphorus compounds. 75. Phosphaalkynes—new building blocks in heterocyclic chemistry. J Heterocyc Chem 31:663–677
Nixon JF (1995) Phospha-alkynes, RC≡P: new building blocks in inorganic and organometallic chemistry. Chem Soc Rev 24:319–328
Bergsträsser U (2004) Product class 6: phosphaalkynes (alkylidynephosphines). Sci Synth 19:427–444
Lynam JM (2007) Recent advances in the chemistry of phosphaalkynes: building blocks for novel organophosphorus compounds. Organomet Chem 33:170–178
Mathey F (2003) Phospha-organic chemistry: panorama and perspectives. Angew Chem Int Ed 42:1578–1604
Wettling T, Schneider J et al (1989) Tetra-tert-butyltetraphosphacubane: the first thermal cyclooligomerization of a phosphaalkyne. Angew Chem Int Ed Engl 28:1013–1014
Fink J, Rösch W et al (1986) 2-Dewar phosphinines—a new class of compounds containing two-coordinate phosphorus. Angew Chem Int Ed Engl 25:280–282
Blatter K, Rösch W et al (1987) Isomerization reactions in the system dewar-phosphinine/phosphaprismane/phosphabenzvalene/phosphinine. Angew Chem Int Ed Engl 26:85–86
Elvers A, Heinemann FW et al (1999) 1-Triorganylstannyl-1,2,4-triphosphole: a versatile starting material for phosphorus-rich cage compounds and π-complexes. Chem Eur J 5:3143–3153
Al-Ktaifani MM, Bauer W et al (2002) Hexaphosphapentaprismane: a new gateway to organophosphorus cage compound chemistry. Chem Eur J 8:2622–2633
Scott LT, DeCicco GJ et al (1983) Decamethyl[5]pericyclyne. A novel homoconjugated cyclic polyacetylene. J Am Chem Soc 105:7760–7761
Scott LT, DeCicco GJ et al (1985) Pericyclynes of order [5], [6], [7], and [8]. Simple convergent syntheses and chemical reactions of the first homoconjugated cyclic polyacetylenes. J Am Chem Soc 107:6546–6555
Scott LT, Cooney MJM (1995) Macrocyclic homoconjugated polyacetylenes. In: Stang PJ, Diederich F (eds) Modern acetylene chemistry, 1st edn. VCH, Weinheim
Diederich F (2001) Carbon-rich acetylenic scaffolding: rods, rings and switches. Chem Commun 219–227
Nielsen MB, Diederich F (2002) The art of acetylenic scaffolding: rings, rods, and switches. Chem Rec 2:189–198
Kivala M, Mitzel F et al (2006) Two-dimensional acetylenic scaffolding: extended donor-substituted perethynylated dehydroannulenes. Chem Asian J 1:479–489
Nielsen MB, Diederich F (2005) Conjugated oligoenynes based on the diethynylethene unit. Chem Rev 105:1837–1867
Maraval V, Chauvin R (2006) From macrocyclic oligo-acetylenes to aromatic ring carbo-mers. Chem Rev 106:5317–5343
Manini P, Amrein W et al (2002) Expanded cubane: synthesis of a cage compound with a C56 core by acetylenic scaffolding and gas-phase transformations into fullerenes. Angew Chem Int Ed 41:4339–4343
Rubin Y, Parker TC et al (1998) Acetylenic cyclophanes as fullerene precursors: formation of C60H6 and C60 by laser desorption mass spectrometry of C60H6(CO)12. Angew Chem Int Ed 37:1226–1229
Tobe Y, Nakagawa N et al (1998) [16.16.16](1,3,5)Cyclophane-tetracosayne (C60H6): a precursor to C60 fullerene. J Am Chem Soc 120:4544–4545
Tobe Y, Nakagawa N et al (2001) Polyyne cyclization to form carbon cages: [16.16.16](1,3,5)Cyclophane-tetracosayne derivatives C60H6 and C60Cl6 as precursor to C60 fullerene. Tetrahedron 57:3629–3636
Yarosh OG, Zhilitskaya LV et al (2005) Novel highly unsaturated macrocyclic and macrobicyclic silahydrocarbons containing Si3H bonds and exocyclic vinyl groups. Russ J Gen Chem 75:1094–1097
Yarosh OG, Zhilitskaya LV et al (2004) Novel acyclic and macrocyclic highly unsaturated silahydrocarbons. Russ J Gen Chem 74:1496–1500
Kwon E, Sakamoto K et al (2004) Synthesis and structures of sila-macrobicyclic compounds: syn and anti isomers of hexasilabicyclo[12.8.8]triacontane. Silicon Chem 1:391–395
Unno M, Saito T et al (2001) Synthesis and crystal structures of silapericyclynes. Bull Chem Soc Jpn 74:2407–2413
Unno M, Negeshi K et al (2001) Extended silapericyclynes. Chem Lett 30:340–341
Unno M, Saito T (1999) Silapericyclyne, (Ph2SiC≡C)6: spontaneous conformational resolution of boat- and chair-‘exploded’ cyclohexane. Chem Lett 28:1235–1236
Voronkov MG, Yarosh OG et al (1990) Highly unsaturated macrocyclic silicohydrocarbons. J Organomet Chem 389:1–22
Bortolin R, Brown SSD et al (1989) Peficyclynosilanes: single crystal X-ray structure of dodecamethyl(6)pericyclynosilane, (Me2SiC≡C)6. Inorg Chim Acta 158:137–139
Hengge E, Baumegger A (1989) Synthese und eigenschaften einiger ethinylsilane. J Organomet Chem 369:C39–C42
Gleiter R, Schäfer W et al (1985) Evidence for a strong σ/π interaction in 3,4,7,8-tetrasilacycloocta-1,5-diyne and 3,4,7,9,11,12-hexasilacyclododecal-1,5,9-triyne. J Am Chem Soc 107:3046–3050
Voronkov MG, Yarosh NO (2003) Cyclogermasilethynes. Russ J Gen Chem 73:1555–1556, for some thiapericyclenes, see ref [18]
Dillon KD, Mathey F et al (1998) Phosphorus, the carbon copy. Wiley, Chichester
Scott LT, Unno M (1990) Novel heterocycles comprising alternating phosphorus atoms and alkyne units. J Am Chem Soc 112:7823–7825
Van Assema SGA, Kraikivskii PB et al (2007) Building blocks for phospha[n]pericyclynes. J Organomet Chem 692:2314–2323
Shiozowa R, Sakamoto K (2003) Synthesis and structures of cyclic ethynylphosphine ligands. Chem Lett 32:1024–1025
Cooney MJM (1993) PhD Dissertation, University of Nevada, Reno
Märkl G, Zollitsch T et al (2000) Polyphospha[m]cyclo[n]carbons (m + n = 15, 20, 25, 30, 40). Chem Eur J 6:3806–3820
Baechler RD, Mislow K (1970) The effect of structure on the rate of pyramidal inversion of acyclic phosphines. J Am Chem Soc 92:3090–3093
Rauk A, Allen LC et al (1970) Pyramidal inversion. Angew Chem Int Ed Engl 9:400–414
Van Assema SGA, De Jong GB et al (2007) Acetylene-substituted phosphane oxides: building blocks for macrocycles. Eur J Org Chem 2405–2412
Laporte F, Mercier F et al (1994) Tetraphosphorus macrocycles from phosphole tetramers. J Am Chem Soc 116:3306–3311
Adams CJ, Bruce ML et al (1993) Cluster chemistry LXXXVII. Some homo- and hetero-nuclear complexes derived from C2(PPh2)2: crystal structures of Re3(μ-H)3(μ-dppa)(CO)10 {dppa = C2(PPh2)2}, Re3(μ-H)3(CO)11{PPh2[μ-C2Ru2(μ-PPh2)(CO)6]} and Os3Ru2(μ5–C2PPh2)(μ-PPh2)(CO)13. J Organomet Chem 447:91–101
Lee J, Humphrey MG (1993) Mixed-metal cluster chemistry. Site-selective reactions of CpWIr3(CO)11 with PPh3 and bidentate phosphines: X-ray crystal structures of CpWIr3(μ-dppe)(μ-CO)3(CO)6, CpWIr3(μ-dppm)(μ-CO)3(CO)6, and CpWIr3(μ-dppa)(μ-CO)3(CO)6. Organometallics 12:3468–3473
Hong FE, Huang YL et al (1999) Preparation of a new cobalt-containing diphosphine ligand and its reaction towards dicobalt octacarbonyl; X-ray crystal structure of [Co2(CO)4(μ-CO)2{μ-P, P-(μ-PPh2C≡CPPh2)Co2(CO)6}]. Inorg Chem Commun 2:450–452
Rodewald D, Schulzke C et al (1995) Alkyne-niobium(I) complexes with functionalized alkynes: synthesis, structure and reactivity. J Organomet Chem 498:29–35
Ward BC, Templeton JL (1980) Nuclear magnetic resonance studies of alkynes as four-electron donor ligands in monomeric tungsten(II) complexes. J Am Chem Soc 102:1532–1538
Melník M, Sundberg M et al (1983) Study of copper(II) propionate adducts with diphenylphosphinoacetylene and bis(diphenylphosphino)acetylene. Acta Chim Scan A 37:659–662
Went MJ (1995) Multidentate ligands bound via alkyne and group 15 or 16 donor sites. Polyhedron 4:465–481
Oberhauser W, Bachman C et al (1997) Binuclear palladium(II), platinum(II) and platinum(IV) complexes containing 1,2-bis(diphenylphosphino)acetylene: different orientations of the diphosphine-bridges due to metal-phosphorus dπ–dπ back bonding. Inorg Chim Acta 256:223–234
Powell AK, Went MJ (1992) Phosphorus donor chemistry of [W(CO)(Ph2PC≡CPPh2)(S2CNEt2)2]. J Chem Soc Dalton Trans 439–445
Nickel TM, Yau SYW et al (1989) A new chelating ligand: co-ordination chemistry of [W(CO)(Ph2PC≡CPPh2)(S2CNEt2)2]. J Chem Soc Chem Commun 775–776
Hong FE, Chang YL et al (2004) Preparation and NMR studies of cobalt-containing diphosphine ligand chelated W, Ru, Au and Pd complexes: Suzuki cross-coupling reactions and carbonylation catalyzed by the Pd complex. Dalton Trans 157–165
Carty AJ, Efraty A (1968) Evidence for metal–phosphorus d π–d π bonding from ν(C≡C) Raman shifts in complexes of bis(diphenylphosphino)acetylene. Chem Commun 1559–1561
Carty AJ, Efraty A (1968) A new class of palladium and platinum complexes: diphosphine bridged M2X4L2 species. (L = bis diphenylphosphinoacetylene). Inorg Nucl Chem Lett 4:427–431
Carty AJ, Efraty A (1969) Coordination complexes of acetylene diphosphines. II. Diphosphine bridged palladium(II) and platinum(II) derivatives. Can J Chem 47:2573–2578
Shin KS, Noh DY (2004) Binuclear platinum(II) building-blocks for the metal-coordinated self-assembly: (dithiolate)Pt(μ-dppa)2Pt(dithiolate) where dppa = bis(diphenylphosphino)acetylene. Bull Korean Chem Soc 25:130–132
Clark HC, Fergusson G et al (1985) Synthesis of heterobimetallic bis(dipheny1phosphino)acetylene-bridged palladium–platinum complexes. Crystal and molecular structure of [PdPtCl4(Ph2PC≡CPPh2)2]·2CHCl3. Inorg Chem 24:3924–3928
Clark HC, Manzer LE (1973) Reactions of (π-1,5-cuclooctadiene)organo-platinum(II) compounds and the synthesis of perfluoroalkylplatinum complexes. J Organomet Chem 59:411–428
Martin-Redondo MP, Scoles L et al (2005) Metal-templated diyne cyclodimerization and cyclotrimerization. J Am Chem Soc 127:5038–5039
Weelock KS, Nelson JH et al (1970) Zerovalent and divalent palladium and platinum complexes with phosphinoacetylenes. Inorg Chim Acta 4:399–403
Xu D, Murfee HJ et al (2000) Photoluminescent macrocyclic Pd(II) and Pt(II) dimeric complexes with Ph2P–C≡C–PPh2 spacer. J Organomet Chem 596:53–63
Clark HC, Kapoor PN et al (1984) Mixed ligand complexes of platinum(0) containing diphosphines. J Organomet Chem 265:107–115
Falvello LR, Fornies J et al (2001) Some platinum(II) complexes containing bis(diphenylphosphino)acetylene PPh2C≡CPPh2: synthesis, characterisation and crystal structures. J Chem Soc Dalton Trans 2132–2140
Praingam N, Anderson GK et al (2007) Base-promoted synthesis of monometallic and bimetallic platinum complexes containing chelating O,O- or S,S-donor ligands. Inorg Chim Acta 360:1767–1770
Bolinger CM, Rauchfuss TB (1982) Template syntheses of 1,2-alkene dichalcogenide chelates via the addition of activated acetylenes to dicyclopentadienyltitanium pentachalcogenides. Inorg Chem 21:3947–3954
Noh DY, Shin KS et al (2007) Synthesis, X-ray crystal structure and luminescence properties of binuclear platinum(II) complex with PtP2S2 core and acetylenic bridge. Bull Korean Chem Soc 28:343–346
Anderson WA, Carty AJ et al (1969) Coordination complexes of acetylene diphosphines. Part III. Silver(I) and mercury(II) complexes. Can J Chem 47:3361–3366
James SL, Xu X et al (2003) Phosphine-based coordination cages and nanoporous coordination polymers. Macromol Symp 196:187–199
Lozano E, Nieuwenhuyzen M et al (2001) Ring-opening polymerisation of silver-diphosphine [M2L3] coordination cages to give [M2L3]∞ coordination polymers. Chem Eur J 7:2644–2651
James SL, Lozano E et al (2000) Triply-bridged diphos disilver helical complexes [Ag2(μ2-dppa-P,P′)3(anion)2] [dppa = bis(diphenylphosphino)acety-lene]. Chem Commun 617–618
Carty AJ, Efraty A et al (1969) Some new diphosphine-bridged nickel carbonyl and cyclopentadienyl compounds. Can J Chem 47:1429–1431
Hogarth G, Norman T (1996) Linking metal centres with bis(diphenylphosphino)acetylene (dppa): syntheses and molecular structures of [{Mo(CO)4(μ-dppa)}2] and [{Mo(CO)3}2(μ-dppa)2]. Polyhedron 15:2859–2867
Baker PK, Armstrong EM (1990) Mono- and dinuclear phosphine coordinated 1,4-bis(diphenylphosphino)ethyne seven-coordinate complexes of molybdenum(II) and tungsten(II). Polyhedron 9:801–804
Howard KE, Rauchfuss TB (1986) Organometallic derivatives of the tetrathiometallates: syntheses, structures, and reactions of MS4[Rh(COD)]2 and MS4[(C5H5)Ru(PPh3)]2 (M = Mo, W). J Am Chem Soc 108:297–299
Peli G, Rizzato S et al (2005) Carbonyl complexes of Rh(I) and Ir(I) and P-donor ligands as useful “building blocks” for the self-assembly of new organometallic polymers. Cryst Eng Commun 7:575–577
Vogels CM, Decken A et al (2006) Rhodium(I) acetylacetonato complexes containing phosphinoalkynes as catalysts for the hydroboration of vinylarenes. Can J Chem 84:146–153
Li L, Reginato N et al (2003) The synthesis and structural characterization of linear and macrocyclic bis(dinitrosyliron) complexes supported by bis(phosphine) bridging ligands. J Can Chem 81:468–475
Eaton GR, Holm RH (1971) Bridged binuclear bis-dithiolene complexes of iron and cobalt. Inorg Chem 10:805–811
Bechtold HC, Rehder D (1979) The coordinative properties of cis/trans-1,4-diphosphabutene and 1,4-diphosphabutyne in carbonylvanadium compounds. J Organomet Chem 172:331–339
Xu D, Khin KT et al (2001) Metallocyclic receptors with ReI/OsII-based moieties: molecular photophysics and selective molecular sensing. Chem Eur J 7:2425–2434
Xu D, Hong B (2000) Investigation of electronic communication and guest inclusion using photoluminescent macrocyclic receptors with RuII centers and Ph2P–C≡C–C≡C–PPh2 spacers. Angew Chem Int Ed 39:1826–1829
Bennett MA, Byrnes MJ et al (2007) Bis(acetylacetonato)ruthenium(II) complexes containing alkynyldiphenylphosphines. Formation and redox behaviour of [Ru(acac)2(Ph2PC≡CR)2] (R = H, Me, Ph) complexes and the binuclear complex cis-[{Ru(acac)2}2(μ-Ph2PC≡CPPh2)}2]. J Chem Soc Dalton Trans 1677–1686
Liu YC, Li CI et al (2006) Syntheses and structural characterization of dicopper(I) bis(diphenylphosphino)acetylene complexes containing tricyclic, cyclic and linear frameworks. Inorg Chim Acta 359:2361–2368
Kui SCF, Kuang JS et al (2006) Self-assembly of a highly stable, topologically interesting metallamacrocycle by bridging gold(I) ions with pyridyl-2,6-diphenyl2- and diphosphanes. Angew Chem Int Ed 45:4663–4666
Viau L, Willis AC et al (2007) Ruthenium cluster chemistry: monodentate bis(diphenylphosphino)acetylene-ligated cluster modules in chain and dendrimer formation. J Organomet Chem 692:2086–2091
Johnson BFG, Sanderson KM et al (2000) Electron-beam induced formation of nanoparticle chains and wires from a ruthenium cluster polymer. Chem Commun 1317–1318
Chen JL, Zhang LY et al (2003) Syntheses, structures, and redox properties of dimeric triruthenium clusters bridged by bis(diphenylphosphino)acetylene and -ethylene. Inorg Chem 43:1481–1490
Housecroft CE, Rheingold AL et al (1998) Towards linked clusters: reactions of [Ru6(CO)17B]-with dppm and [ClAu(L–L)AuCl] (L–L=bis(diphenylphosphino)-alkanes, -ethene and -ethyne, and the crystal structure of [HRu6(CO)15(P,P′-dppm)B] (dppm=bis(diphenylphosphino)methane). J Organomet Chem 565:105–114
Adams CJ, Bruce MI et al (1998) Carbonyl substitution reactions of ruthenium cluster complexes containing dicarbon (C2) ligands: X-ray structures of Ru5(μ5–C2)(μ-SMe)2(μ-PPh2)2(CO)10(L) [L=CNBut, P(OMe)3]. J Organomet Chem 561:97–107
Bruce MI, Humphrey PA et al (1997) Acetylenic phosphines bridging two cluster units: molecular structure of {Ru3(μ-H)(μ3–C2But)(CO)8}2(μ-dppa) [dppa = C2(PPh2)2]. Austr J Chem 50:535–538
Louattani E, Suades J et al (1996) Synthesis of a zwitterionic P-coordinated complex with bis(diphenylphosphino)acetylene. Organometallics 15:468–471
Osella D, Hanzlík J (1993) Electronic interactions in multicluster arrays. An electrochemical approach. Part III. Inorg Chim Acta 213:311–317
Sappa E (1988) Bis(diphenylphosphino)acetylene as a bridging ligand between homo- and hetero-metallic clusters. J Organomet Chem 352:327–336
Bettenhausen M, Eichhöfer A et al (1999) Synthese und strukturen neuer selenido- und selenolatoverbrückter kupfercluster: [Cu38Se13(SePh)12(dppb)6] (1), [Cu(dppp)2][Cu25Se4(SePh)18(dppp)2] (2), [Cu36Se5(SePh)26(dppa)4] (3), [Cu58Se16(SePh)24(dppa)6] (4) und [Cu3(SeMes)3(dppm)] (5). Z Anorg Allg Chem 625:593–601
Semmelmann M, Fenske D et al (1998) Copper-chalcogenide clusters stabilised with linear bidentate phosphine ligands. J Chem Soc Dalton Trans 2541–2545
Sevillano P, Fuhr O et al (2007) Synthese und struktur von [Au10Se5(dppa)4{Co2(CO)5}4]. Z Anorg Allg Chem 633:1783–1786
Amoroso AJ, Johnson BFG et al (1992) The use of bis(diphenylphosphinoacetylene) and its digold derivative as linking groups in osmium cluster chemistry. Crystal structures of [{Os3(CO)11}2(dppa)], [Os3(CO)10(dppa)]2 and [Os4H(CO)12Au(dppa)]2 (dppa = Ph2PC≡CPPh2). J Organomet Chem 440:219–231
Johnson BFG, Lewis J et al (1990) Synthesis and characterisation of linked triosmium clusters using the bis(diphenylphosphino)acetylene ligand. J Organomet Chem 397:C28–C30
Amoroso AJ, Lewis J et al (1993) Mixed-metal clusters containing osmium and gold. In: Welch AJ, Chapman SK (eds) The chemistry of the copper and zinc triads, 1st edn. Royal Society of Chemistry, Cambridge
Galsworthy JR, Housecroft CE et al (1995) Unexpected gold-containing boride clusters formed from the reactions of [RhRu3H(η5-C5Me5)(CO)9BH]− with gold(I) phosphine derivatives: crystal structures of [RhRu3H(η5-C5Me5)(CO)9B {Au(PPh3)}2(AuCl)]·CH2Cl2 and [RhRu3H(η5-C5Me5)(CO)9B{Au2(dppf)} (AuCl)]·CH2Cl2 [dppf = 1,1′-bis(diphenylphosphino)ferrocene]. J Chem Soc Dalton Trans 2639–2647
Hong FE, Chang H et al (2001) Preparation and characterization of a cyclic compound consisting of bis(diphenylphosphino)acetylene joined alkyne-bridged dicobalt fragments. Chem Lett 30:1130–1131
Aullón G, Hamidi M et al (2004) Chalcogen-chalcogen bonds in edge-sharing Square-planar d8 complexes. Are they possible? Inorg Chem 43:3702–3714
Nicolaou KC, Smith AL (1995) The enediyne antibiotics. In: Stang PJ, Diederich F (eds) Modern acetylene chemistry, 1st edn. VCH, Weinheim
Nicolaou KC, Zuccarello G et al (1988) Cyclic conjugated enediynes related to calicheamicins and esperamicins: calculations, synthesis, and properties. J Am Chem Soc 110:4866–4868
Basak A, Mandal S et al (2003) Chelation-controlled Bergman cyclization: synthesis and reactivity of enediynyl ligands. Chem Rev 103:4077–4094
Warner BP, Millar SP et al (1995) Controlled acceleration and inhibition of Bergman cyclization by metal chlorides. Science 269:814–816
Nicolaou KC, Dai WM (1991) Chemistry and biology of the enediyne anticancer antibiotics. Angew Chem Int Ed Engl 30:1387–1416
Coalter NL, Concolino TE et al (2000) Structure and thermal reactivity of a novel Pd(0) metalloenediyne. J Am Chem Soc 122:3112–3117
Schmitt EW, Huffmann JC et al (2001) Thermal reactivities of isostructural d10 metalloenediynes: metal-dependent Bergman cyclization. Chem Commun 167–168
Baumgartner T, Huynh K et al (2002) Metallochain cluster complexes and metallomacrocyclic triangles based on coordination bonds between palladium or platinum and diphosphinoacetylene ligands. Chem Eur J 8:4622–4632
Carty AJ, Efraty A (1968) Binuclear copper(I) complexes with bridging bis(diphenylphosphino)acetylene groups. Can J Chem 46:1598–1599
Carty AJ, Efraty A (1969) Coordination complexes of acetylene diphosphines. I. diphosphine-bridged binuclear copper(I) and gold(I) complexes of bis(diphenylphosphino)acetylene. Inorg Chem 8:543–550
Wallbank AI, Corrigan JF (2002) Triply bridged dicopper-bis(trimethylsilylchalcogenolates): synthesis and characterization of the series of helical complexes [(Me3SiE-Cu)2(μ-Ph2PC≡CPPh2-κ2 P)3] (E = S, Se, Te). Can J Chem 80:1592–1599
DeGroot MW, Corrigan JF (2006) Metal-chalcogenolate complexes with silyl functionalities: synthesis and reaction chemistry. Z Anorg Allg Chem 632:19–29
Bardaji M, De la Cruz MT et al (2005) Luminescent dinuclear gold complexes of bis(diphenylphosphano)acetylene. Inorg Chim Acta 358:1365–1372
Yeh WY, Peng SM et al (2003) Synthesis and reactivity of ditungsten helical complex W2(CO)6(μ-Ph2PC≡CPPh2)3. J Organomet Chem 671:145–149
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2011 Springer Science+Business Media B.V.
About this chapter
Cite this chapter
Weymiens, W., Slootweg, J.C., Lammertsma, K. (2011). Phosphine Acetylenic Macrocycles and Cages: Synthesis and Reactivity. In: Peruzzini, M., Gonsalvi, L. (eds) Phosphorus Compounds. Catalysis by Metal Complexes, vol 37. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-3817-3_2
Download citation
DOI: https://doi.org/10.1007/978-90-481-3817-3_2
Published:
Publisher Name: Springer, Dordrecht
Print ISBN: 978-90-481-3816-6
Online ISBN: 978-90-481-3817-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)