RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2006(2): 293-298
DOI: 10.1055/s-2005-918512
DOI: 10.1055/s-2005-918512
PAPER
© Georg Thieme Verlag Stuttgart · New York
New Route to Unsymmetrical 9,10-Disubstituted Ethynylanthracene Derivatives
Weitere Informationen
Received
6 July 2005
Publikationsdatum:
21. Dezember 2005 (online)
Publikationsverlauf
Publikationsdatum:
21. Dezember 2005 (online)
Abstract
The preparation of new organic compounds bearing ethynylanthracene fragments is described, and an original pathway for the selective synthesis of unsymmetrical 9,10-diethynylanthracenes is given. The synthesis of some 9-ethynyl-10-substituted anthracene derivatives is also reported.
Key words
anthracenes - alkyne ligands - C-C coupling - synthesis design
-
1a
Roué S.Lapinte C. J. Organomet. Chem. 2005, 690: 594 -
1b
Courmarcel J.Le Gland G.Toupet L.Paul F.Lapinte C. J. Organomet. Chem. 2003, 670: 108 -
1c
Le Stang S.Lenz D.Paul F.Lapinte C. J. Organomet. Chem. 1999, 572: 189 - 2
Sonogashira K.Tohga Y.Hagihara N. Tetrahedron Lett. 1975, 50: 4467 -
3a
Inouye M.Konishi T.Isagawa K. J. Am. Chem. Soc. 1993, 115: 8091 -
3b
Butler IR.Callabero AG.Kelly GA.Amey JR.Kraemer T.Thomas DA.Gelbrich T.Coles SJ. Tetrahedron Lett. 2004, 45: 467 -
3c
Kaway T.Sasaki T.Irie M. Chem. Commun. 2001, 711 -
3d
Manhart SA.Adachi A.Sakamaki K.Okita K.Ohshita J.Ohno T.Hamaguchi T.Kunai A.Kido J. J. Organomet. Chem. 1999, 592: 52 -
3e
Godinez CE.Zepeta G.Garcia-Garibay MA. J. Am. Chem. Soc. 2002, 124: 4701 -
3f
Nguyen P.Todd S.Van den Boggelaar D.Taylor NJ.Marder TB.Wittmann F.Friend RH. Synlett 1994, 299 -
3g
Danel K.T’suen Lin J. Arkivoc 2002, (i): 12 -
3h
Lambert C.Nöll G.Schelter J. Nat. Mater. 2002, 1: 69 -
3i
Fraysse S.Coudret C.Launay J.-P. J. Am. Chem. Soc. 2003, 125: 5880 -
3j
El-Ghayoury A.Harriman A.Khatyr A.Ziessel R. J. Phys. Chem. A 2000, 104: 1512 -
3k
Khan MS.Al-Mandhary MRA.Al-Suti MK.Al-Battashi FR.Al-Saadi S.Ahrens G.Bjernemose JK.Mahon MF.Raithby PR.Younus M.Chawdhury N.Köhler A.Marseglia EA.Tedesco E.Feeder N.Teat SJ. Dalton Trans. 2004, 2377 - 4
Duerr BF.Chung T.-S.Czarnik AW. J. Org. Chem. 1988, 53: 2120 -
5a
Yang WJ.Kim CH.Jeong M.-Y.Lee SK.Piao MJ.Jeon S.-J.Cho BR. Chem. Mater. 2004, 16: 2783 -
5b
Kilså K.Macpherson AN.Gillbro T.Mårtensson J.Albinsson B. Spectrochim. Acta, Part A 2001, 57: 2213 -
5c
Kaneko T.Makino T.Miyaji H.Teraguchi M.Aoki T.Miyasaka M.Nishide H. J. Am. Chem. Soc. 2003, 125: 3554 -
5d
Kaneko T.Makino T.Miyaji H.Onuma A.Teraguchi M.Aoki T. Polyhedron 2003, 22: 1845 -
5e
Swager TM.Gil CJ.Wrighton MS. J. Phys. Chem. 1995, 99: 4886 -
5f
Malakhov AD.Skorobogatyi MV.Prokhorenko IA.Gontarev SV.Kozhich DT.Stetsenko DA.Stepanova IA.Shenkarev ZO.Berlin YA.Korshun VA. Eur. J. Org. Chem. 2004, 1298 -
5g
Piet JJ.Taylor PN.Anderson HL.Osuka A.Warman JM. J. Am. Chem. Soc. 2000, 122: 1749 -
5h
Wan C.-W.Burghart A.Chen J.Bergström F.Johansson L.Wolford MF.Kim TG.Topp MR.Hochstrasser RM.Burgess K. Chem.-Eur. J. 2003, 9: 4430 - 6
Kuhn R.Fischer H. Chem. Ber. 1961, 94: 3060 - 7
Gore PH.Gupta SD.Obaji GA. J. Prakt. Chem. 1984, 326: 381 -
8a
Olah GA.Singh BP.Liang G. J. Org. Chem. 1984, 49: 2922 -
8b
Yamaguchi S.Akiyama S.Tamao K. J. Am. Chem. Soc. 2000, 122: 6335 -
8c
Lehmkuhl H.Mehler K.Benn R.Rufinska A.Schroth G.Krüger C. Chem. Ber. 1984, 117: 389 -
8d
Engman L.Hellberg JSE. J. Organomet. Chem. 1985, 296: 357 -
8e
Abdul Karim SM.Nomura R.Sanda F.Seki S.Watanabe M.Masuda T. Macromolecules 2003, 36: 4786 - 9
Corey EJ.Fuchs PL. Tetrahedron Lett. 1972, 36: 3769 -
10a
Dolhem F.Lièvre C.Demailly G. Tetrahedron Lett. 2002, 43: 1847 -
10b
Michel P.Rassat A. Tetrahedron Lett. 1999, 40: 8579 -
10c
Shen W.Thomas SA. Org. Lett. 2000, 2: 2857 -
10d
Shen W.Kunzer A. Org. Lett. 2002, 4: 1315 -
10e
Huh DH.Jeong JS.Lee HB.Ryu H.Kim YG. Tetrahedron 2002, 58: 9925 - 11
Hwang GT.Son HS.Ku JK.Kim BH. J. Am. Chem. Soc. 2003, 125: 11241 - 12
Lavastre O.Ollivier L.Dixneuf PH. Tetrahedron 1996, 52: 5495 - 13
Xue J.-Y.Parker VD. J. Org. Chem. 1994, 59: 6564 - See for example:
-
14a
Erman MB.Snow JW.Williams MJ. Tetrahedron Lett. 2000, 41: 6749 -
14b
Talukdar S.Hsu J.-L.Chou T.-C.Fang J.-M. Tetrahedron Lett. 2001, 42: 1103 -
14c
Bose DS.Narsaiah AV. Tetrahedron Lett. 1998, 39: 6533 -
14d
Wang E.-C.Lin G.-J. Tetrahedron Lett. 1998, 39: 4047 -
14e
Villemin D.Lalaoui M.Ben Alloum A. Chem. Ind. (London) 1991, 176 - 15
Attanasi O.Palma P.Serra-Zanetti F. Synthesis 1983, 741