Atom-economic, metal- and halogen-free synthesis of podands: α,ω-diphosphines and their chalcogenides separated by alkane diol spacers

Synthesis (Germany)

Volumn 44, Issue 18, 2012, Pages 2938-2946

  Oparina, Ludmila A ^a   Gusarova, Nina K ^a   Vysotskaya, Oksana V ^a   Kolyvanov, Nikita A ^a   Artem'Ev, Alexander A ^a   Trofimov, Boris A ^a  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

Author keywords

addition; alkenes; ethers; phosphorylation; radical reactions

Indexed keywords

ADDITION; ALKANEDIOLS; DIPHOSPHINES; DIVINYL ETHER; HALOGEN-FREE; MOLAR RATIO; RADICAL REACTIONS; SECONDARY PHOSPHINES; UV IRRADIATION;

BUTADIENE; CHALCOGENIDES; ETHERS; OLEFINS; ORGANIC COMPOUNDS; PHOSPHORUS COMPOUNDS; PHOSPHORYLATION; REACTION KINETICS;

PARAFFINS;

12,12 DIPHENYL 12 THIOXO 3,6,9 TRIOXO 12 LAMBDA PHOSPHADODECYL(DIPHENYL)PHOSPHINE SULFIDE; 2 [2 (DIPHENETHYLPHOSPHINO)ETHOXY]ETHYL 2 (DIPHENYLPHOSPHINO)ETHYL ETHER; 2 [2 (DIPHENYLPHOSPHINO)ETHOXY]ETHYL 2 (DIPHENYLPHOSPHINO)ETHYL ETHER; 2 [2 [2 (DIHPENETHYLPHOSPHORYL)ETHOXY]ETHOXY]ETHYL(DIPHENETHYL)PHOSPHINE SULFIDE; 2 [2 [2 (DIPHENETHYLPHOSPHINO)ETHOXY]ETHOXY]ETHYL 2 (DIPHENETHYLPHOSPHINO)ETHYL ETHER; 2 [2 [2 (DIPHENETHYLPHOSPHOROSELENOYL)ETHOXY]ETHOXY]ETHYL(DIPHENETHYL)PHOSPHINE SELENIDE; 2 [2 [2 (DIPHENETHYLPHOSPHOROTHIOYL)ETHOXY]ETHOXY]ETHYL(DIPHENETHYL)PHOSPHINE SULFIDE; 2 [2 [2 (DIPHENYLPHOSPHINO)ETHOXY]ETHOXY]ETHYL 2 (DIPHENYLPHOSPHINO)ETHYL ETHER; 2 [2 [2 (DIPHENYLPHOSPHOROTHIOYL)ETHOXY] 1 METHYLETHOXY]ETHYL(DIPHENETHYL)PHOSPHINE SULFIDE; 2 [2 [2 (DIPHENYLPHOSPHOROTHIOYL)ETHOXY]ETHOXY]ETHYL(DIPHENYL)PHOSPHINE SULFIDE; 2 [2 [2 [BIS(4 CHOLOROPHENETHYL)PHOSPHINO]ETHOXY]ETHOXY]ETHYL 2 [BIS(4 CHLOROPHENETHYL)PHOSPHINO]ETHYL ETHER; 2 [2 BIS[2 (2 FURYL)ETHYL]PHOSPHINOETHOXY]ETHYL 2 BIS [2 (2 FURYL)ETHYL]PHOSPHINOETHYL ETHER; 2 [3 [2 (DIHPENETHYLPHOSPHOROTHIOYL)ETHOXY]BUTOXY]ETHYL(DIPHENETHYL)PHOSPHINE SULFIDE; 2 [3 [2 (DIHPENETHYLPHOSPHOROTHIOYL)ETHOXY]PROPOXY]ETHYL(DIPHENETHYL)PHOSPHINE SULFIDE; 2 [4 [2 (DIHPENETHYLPHOSPHOROSELENOYL)ETHOXY]BUTOXY]ETHYL(DIPHENETHYL)PHOSPHINE SULFIDE; 2 [4 [2 (DIHPENETHYLPHOSPHOROTHIOYL)ETHOXY]BUTOXY]ETHYL(DIPHENETHYL)PHOSPHINE SULFIDE; 2 [6 [2 (DIHPENETHYLPHOSPHOROSELENOYL)ETHOXY]BUTOXY]ETHYL(DIPHENETHYL)PHOSPHINE SULFIDE; 2 [6 [2 (DIHPENETHYLPHOSPHOROTHIOYL)ETHOXY]HEXYLOXY]ETHYL(DIPHENETHYL)PHOSPHINE SULFIDE; ALPHA OMEGA DIPHOSPHINE DERIVATIVE; DIPHENETHYL(12 PHENETHYL 14 PHENYL 12 THIOXO 3,6,9 TRIOXA 12LAMBDA PHOSPHATETRADECYL)PHOSPHINE SULFIDE; DIPHENETHYL(15 PHENETHYL 17 PHENYL 15 SELENOXO 3,6,9,12 TETRAOXA 15LAMBDA PHOSPHAHEPTADECYL)PHOSPHINE SULFIDE; DIPHENETHYL(15 PHENETHYL 17 PHENYL 15 THIOXO 3,6,9,12 TETRAOXA 15LAMBDA PHOSPHAHEPTADECYL)PHOSPHINE SULFIDE; DIPHOSPHINE CHALCOGENIDE DERIVATIVE; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL INTERACTION; CHEMICAL PARAMETERS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; MARKOVNIKOV DIADDUCT REACTION; RADICAL REACTION; STEREOCHEMISTRY; SYNTHESIS; ULTRAVIOLET IRRADIATION;

EID: 84866072009     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1316764     Document Type: Article

References (72)

1. Knowles WS. Angew. Chem. Int. Ed.: 2002; 41 1998
2. Klabunovskii EI. Katal. Prom. (in Russian): 2006; 52
3. Doucet H. Eur. J. Org. Chem.: 2008; 2013
4. Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications. Börner A. Wiley-VCH Weinheim: 2008; 1
5. Freixa Z, van Leeuwen PW. N. M. Coord. Chem. Rev.: 2008; 252 1755
6. Birkholz MN, Freixa Z, van Leeuwen PW. N. M. Chem. Soc. Rev.: 2009; 38 1099
7. Chatterjee S, Patel SK, Tirkey V, Mobin SM. J. Organomet. Chem.: 2012; 699 12
8. Dutta DK, Chutia P, Woollins JD, Slawin AM. Z. Inorg. Chim. Acta: 2006; 359 877
9. Dutta DK, Woollins JD, Slawin AM. Z, Konwar D, Sharma M, Bhattacharyya P, Aucott SM. J. Organomet. Chem.: 2006; 691 1229
10. Deb B, Sarmah PP, Dutta DK. Eur. J. Inorg. Chem.: 2010; 1710
11. Deb B, Dutta DK. J. Mol. Catal. A: Chem.: 2010; 326 21
12. Dutta DK, Deb B. Coord. Chem. Rev.: 2012; 255 1686
13. Aizawa S, Kondo M, Miyatake R, Tamai M. Inorg. Chim. Acta: 2007; 360 2809
14. Aizawa S, Tamai M, Sakuma M, Kubo A. Chem. Lett.: 2007; 36 130
15. Berners-Price SJ, Sadler PJ. Phosphines and metal phosphine complexes: relationship of chemistry to anticancer and other biological activity. Springer-Verlag Berlin: 1988; 102
16. Rackham O, Nichols SJ, Leedman PJ, Berners-Price SJ, Filipovska A. Biochem. Pharmacol.: 2007; 74 992
17. Kodama H, Owatari K, Chara N, Nakatsui K, Kaneda Y. JP 308437: 2007;; Chem. Abstr. 2008, 148, 33892v.
18. Kodama H, Ohto K, Oohara N, Nakatsui K, Kaneda Y. Int. Appl. WO 139176: 2007;; Chem. Abstr. 2008, 148, 33888y.
19. Tian S, Siu F.-M, Kiu SC. F, Lok C.-N, Che C.-M. Chem. Commun.: 2011; 47 9318
20. Wetzel C, Kunz PC, Kassack MU, Hamacher A, Böhler Ph, Watjen W, Ott I, Rubbiani R, Spingler B. Dalton Trans.: 2011; 9212
21. Ha-Thi MH, Penhoat M, Michelet V, Leray I. Org. Lett.: 2007; 9 1133
22. Smith C, Mann KR. Chem. Mater.: 2009; 21 5042
23. Smith CS, Branham CW, Marquardt BJ, Mann KR. J. Am. Chem. Soc.: 2010; 132 14079
24. Mangalum A, Smith RC. Dalton Trans.: 2010; 5145
25. Gauzzi D, Graiff C, Massera C, Predieri G, Tiripicchio A. Inorg. Chim. Acta: 2000; 471 300
26. Gauzzi D, Graiff C, Massera C, Predieri G, Tiripicchio A. J. Cluster Sci.: 2001; 12 259
27. Belletti D, Graiff C, Lostao V, Pattacini R, Predieri G, Tiripicchio A. Inorg. Chim. Acta: 2003; 347 137
28. Turanov AN, Karandashev VK, Baulin VE, Yarkevich AN, Safronova ZV. Solv. Extr. Ion Exch.: 2009; 27 551
29. Nogami M, Sugiyama Y, Ikeda Y. J. Radioanal. Nucl. Chem.: 2010; 284 195
30. Wetzel C, Kunz PC, Kassack MU, Hamacher A, Böhler Ph, Watjen W, Ott I, Rubbiani R, Spingler B. Dalton Trans.: 2011; 9212
31. Warad I, Al-Othman Z, Al-Resayes S, Al-Deyab S, Kenawy E. Molecules: 2010; 15 1028
32. Warad I, Al-Resayes S, Al-Othman Z, Al-Deyab SS, Kenawy ER. Molecules: 2010; 15 3618
33. Warad I, Al-Far R, Al-Resayes S, Boshaala A, Hammouti B. Inter. J. Phys. Sci.: 2011; 6 7183
34. Karasik AA, Sinyashin OG. Phosphorus Based Macrocyclic Ligands: Synthesis and Applications In Catalysis by Metal Complexes. Phosphorus Compounds: Advanced Tools in Catalysis and Material Sciences. Gonsalvi L, Peruzzini M. Springer Dordrecht: 2011; 37 377
35. Xu FB, Zhang LF, Sun LJ, Xuan ZA, Zhang ZZ, Zhao WJ. Chin. J. Chem.: 2000; 18 729
36. Markl G, Reisinger J, Kreitmeier P, Langer J, Noth H. Helv. Chim. Acta: 2002; 85 1714
37. Bolzati C, Boschi A, Uccelli L, Tisato F, Refosco F, Cagnolini A, Duatti A, Prakash S, Bandoli G, Vittadini A. J. Am. Chem. Soc.: 2002; 124 11468
38. Song LC, Yu GA, Wang HT, Su FH, Hu QM, Song YL, Gao YC. Eur. J. Inorg. Chem.: 2004; 866
39. Major Q, Lough AJ, Gusev DG. Organometallics: 2005; 24 2492
40. Varshney A, Gray GM. Inorg. Chem.: 1991; 30 1748
41. Varshney A, Webster ML, Gray GM. Inorg. Chem.: 1992; 31 2580
42. Gray GM, Duffey CH. Organometallics: 1994; 13 1542
43. Gray GM. Comments Inorg. Chem.: 1995; 17 95
44. Gray GM, Varshney A, Duffey TH. Organometallics: 1995; 14 238
45. Gray GM, Duffey CH. Organometallics: 1995; 14 245
46. Gray GM. Comments Inorg. Chem.: 1995; 17 95
47. Gray GM, Fish FP, Duffey CH. Inorg. Chim. Acta: 1996; 246 229
48. Stang PJ, Cao DH, Chen K, Gray GM, Muddiman DC, Smith RD. J. Am. Chem. Soc.: 1997; 119 5163
49. Smith DC. Jr, Gray GM. Inorg. Chem.: 1998; 37 1791
50. Duffey CH, Lake CH, Gray GM. Organometallics: 1998; 17 3550
51. Hariharasarma M, Gray GM. J. Chem. Crystallogr.: 1998; 28 297
52. Smith DC. Jr, Lake CH, Gray GM. Chem. Commun.: 1998; 2771
53. Hariharasarma M, Lake CH, Watkins CL, Gray GM. J. Organomet. Chem.: 1999; 580 328
54. Smith DC. Jr, Gray GM. J. Chem. Soc., Dalton Trans.: 2000; 677
55. Gray GM, Smith DC. Jr, Duffey CH. Inorg. Chim. Acta: 2000; 300-302 581
56. Duffey CH, Lake CH, Gray GM. Inorg. Chim. Acta: 2001; 317 199
57. Smith DC, Lake CH, Gray GM. Dalton Trans.: 2003; 2950
58. Owens SB, Smith DC, Lake CH, Gray GM. Eur. J. Inorg. Chem.: 2008; 4710
59. Owens SB, Gray GM. Organometallics: 2008; 27 4282
60. Sawamura M, Ito Y. Chem. Rev.: 1992; 92 857
61. Nataro C, Baseski H, Thomas CM, Wiza BJ, Rourke KM. Polyhedron: 2001; 20 1023
62. Trofimov BA, Kudyakova RN, Oparina LA, Parshina LN, Vins VV. Zh. Prikl. Khim. (Leningrad): 1991; 64 873
63. Oparina LA, Khil'ko MYa, Chernysheva NA, Shaikhudinova SI, Parshina LN, Preiss Th, Henkelmann J, Trofimov BA. Russ. J. Org. Chem.: 2005; 41 661
64. Trofimov BA, Atavin AS, Gavrilova GA, Kalabin GA. Zh. Obshch. Khim.: 1968; 38 2344
65. Atavin AS, Trofimov BA, Gavrilova GA, Korataeva IM. Zh. Obshch. Khim.: 1971; 41 804
66. Healy MP, Parsons AF, Rawlinson JG. T. Org. Lett.: 2005; 7 1597
67. Trofimov BA, Malysheva SF, Belogorlova NA, Kuimov VA, Albanov AI, Gusarova NK. Eur. J. Org. Chem.: 2009; 3427
68. Oparina LA, Malysheva SF, Gusarova NK, Belogorlova NA, Vysotskaya OV, Stepanov AV, Albanov AI, Trofimov BA. Synthesis: 2009; 3427
69. Gusarova NK, Malysheva SF, Oparina LA, Belogorlova NA, Tantsyrev AP, Parshina LN, Sukhov BG, Tlegenov RT, Trofimov BA. ARKIVOC: 2009; (vii) 260
70. Gusarova NK, Bogdanova MV, Ivanova NI, Chernysheva NA, Sukhov BG, Sinegovskaya LM, Kazheva ON, Alexandrov GG, Dyachenko OA, Trofimov BA. Synthesis: 2005; 3103
71. Sukhov BG, Gusarova NK, Ivanova NI, Bogdanova MV, Kazheva ON, Alexandrov GG, Dyachenko OA, Sinegovskaya LM, Malysheva SF, Trofimov BA. J. Struct. Chem.: 2005; 46 1066
72. Malysheva SF, Artem'ev AV, Gusarova NK, Timokhin BV, Tatarinova AA, Trofimov BA. Russ. J. Gen. Chem.: 2009; 79 1617