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Synthesis 2002(12): 1747-1751
DOI: 10.1055/s-2002-33644
DOI: 10.1055/s-2002-33644
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of 2-Benzyl-1,10-phenanthrolines
Substituted by Sulfoxide or
Sulfone Groups as Potential
Photochromic Compounds
Further Information
Received
3 April 2002
Publication Date:
05 September 2002 (online)
Publication History
Publication Date:
05 September 2002 (online)
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Abstract
New 2-benzyl-1,10-phenanthrolines, substituted at the 2′ position by electron-withdrawing groups, were synthesized through nucleophilic substitution involving 2-chloro-1,10-phenanthroline and substituted benzyllithiums, respectively. The expected reversible photoinduced proton transfer reaction of such compounds were studied.
Key words
benzylation - heterocycles - metalations - sulfones - photochemistry
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1a
Shinohara S.Takeda J.Ooike T.Kurita S. J. Phys. Soc. Jpn. 1999, 68: 1725 -
1b
Houbrechts S.Clays K.Persoons A.Pikramenou Z.Lehn JM. Chem. Phys. Lett. 1996, 258: 485 -
1c
Corval A.Kuldova K.Eichen Y.Pikramenou Z.Lehn JM.Trommsdorff HP. J. Phys. Chem. 1996, 100: 19315 -
1d
Frank I.Grimme S.Peyerimhoff SD. J. Phys. Chem. 1996, 100: 16187 -
1e
Scherl M.Haarer D.Fischer J.Decian A.Lehn JM.Eichen Y. J. Phys. Chem. 1996, 100: 16175 -
1f
Eichen Y.Lehn JM.Scherl M.Haarer D.Caselegno R.Corval A.Kuldova K.Trommsdorff HP. J. Chem. Soc., Chem. Commun. 1995, 713 -
2a
Hardwick R.Mosher HS.Passailaigue P. J. Chem. Soc., Faraday Trans. 1960, 56: 44 -
2b
Klemm D.Klemm E. J. Prackt. Chem. 1978, 320: 551 - 3
Heynderickx A.Samat A.Guglielmetti R. J. Heterocycl. Chem. 2001, 38: 737 - 4
Taylor EC.Martin SF. J. Am. Chem. Soc. 1974, 96: 8095 - 5
Corey EJ.Borror AL.Foglia T. J. Org. Chem. 1965, 30: 288 - 6
Sigman DS.Wahl GM.Creighton DJ. Biochemistry 1972, 11: 2236 - 7
Taylor DB.Callahan KP.Shaikh I. J. Med. Chem. 1975, 18: 1088 - 8
Mathis JM.Pallenberg AJ. Synth. Commun 1997, 27: 2943 -
9a
Lüning U.Müller M. Chem. Ber. 1990, 123: 643 -
9b
Solladié N.Chambron JC.Sauvage JP. J. Am. Chem. Soc. 1999, 121: 3684 -
10a
Johnson MR.Bell D.Shanaman L. Heterocycles 1997, 45: 1059 -
10b
Fife TH.Pujari MP. J. Am. Chem. Soc. 1988, 110: 7790 - 11
Labadie JW.Stille JK. J. Am. Chem. Soc. 1983, 105: 6129 - 12
Desponds O.Schlosser M. J. Organomet. Chem. 1991, 409: 93 - 13
Meyer JJ.Levoir P.Dubest R. Analyst (Cambridge U. K.) 1995, 120: 447