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Synthesis 2009(16): 2773-2777
DOI: 10.1055/s-0029-1217601
DOI: 10.1055/s-0029-1217601
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis and Electrochemical Signature of Novel Norbornyl-ferrocene Hybrids
Further Information
Received
2 March 2009
Publication Date:
10 July 2009 (online)
Publication History
Publication Date:
10 July 2009 (online)
Abstract
Novel norbornyl-ferrocene hybrids have been synthesized in excellent yields via Diels-Alder reactions between 1,2,3,4-tetrahalo-5,5-dimethoxycyclopentadiene and vinyl- or acryloylferrocenes. Halogen reduction of vinylferrocene adducts followed by catalytic hydrogenation afforded ferrocenyl-norbornane. Hybrids showed the dependence of the redox potential on the nature of the substituents on the norbornyl moiety.
Key words
Diels-Alder reaction - ferrocene - radical hydrodehalogenation - reduction - electrochemical study
-
1a
Long NJ. Angew. Chem., Int. Ed. Engl. 1995, 34: 21 -
1b
Balavoine GGA.Daran J.-C.Iftime G.Lacroix PG.Manoury E.Delaire JA.Maltey-Fanton I.Nakatani K.Bella SD. Organometallics 1999, 18: 21 -
2a
Togni A.Hayashi T. Ferrocenes VCH; Weinheim: 1995. -
2b
You S.-L.Hou X.-L.Dai L.-X.Yu Y.-H.Xia W. J. Org. Chem. 2002, 67: 4684 -
2c
Pu L.Yu H.-B. Chem. Rev. 2001, 101: 757 -
3a
Sawamura M.Kuninobu Y.Toganoh M.Matsuo Y.Yamanaka M.Nakamura E. J. Am. Chem. Soc. 2002, 124: 9354 -
3b
Yuan WZ.Sun JZ.Liu JZ.Dong Y.Li Z.Xu HP.Qin A.Häussler M.Jin JK.Zheng Q.Tang BZ. J. Phys. Chem. B 2008, 112: 8896 -
4a
Casas-Solvas JM.Vargas-Berenguel A.Capitán-Vallvey LF.Santoyo-González F. Org. Lett. 2004, 6: 3687 ; and references therein -
4b
Casas-Solvas JM.Ortiz-Salmerón E.García-Fuentes L.Vargas-Berenguel A. Org. Biomol. Chem. 2008, 6: 4230 - 5
Martínez R.Ratera I.Tárraga A.Molina P.Veciana J. Chem. Commun. 2006, 3809 - 6
Khan FA.Prabhudas B.Dash J. J. Prakt. Chem. 2000, 342: 512 - For selected examples, see:
-
7a
Khan FA.Sudheer Ch. Org. Lett. 2008, 10: 3029 -
7b
Khan FA.Upadhyay SK. Tetrahedron Lett. 2008, 49: 6111 -
7c
Khan FA.Rout B. J. Org. Chem. 2007, 72: 7011 -
7d
Khan FA.Rout B. Tetrahedron Lett. 2006, 47: 5251 -
7e
Khan FA.Rao CN. Tetrahedron Lett. 2006, 47: 7567 -
7f
Khan FA.Dash J.Sudheer Ch.Sahu N.Parasuraman K. J. Org. Chem. 2005, 70: 7565 -
7g
Khan FA.Dash J. Eur. J. Org. Chem. 2004, 2692 -
7h
Khan FA.Dash J.Sudheer Ch. Chem. Eur. J. 2004, 10: 2507 -
7i
Khan FA.Satapathy R.Dash J.Savitha G. J. Org. Chem. 2004, 69: 5295 -
8a
Prokesova M.Solcaniova E.Toma S.Muir KW.Torabi AA.Konox GR. J. Org. Chem. 1996, 61: 3392 -
8b
Prokesova M.Rihs G.Toma S. Collect. Czech. Chem. Commun. 1996, 61: 364 -
9a
Carroll MA.White AJP.Widdowson DA.Williams DJ. J. Chem. Soc., Perkin Trans. 1 2000, 1551 -
9b
Lo Sterzo C.Ortaggi G. J. Chem. Soc., Perkin Trans. 2 1984, 345 - 10
Turbitt TD.Watts WE. J. Organomet. Chem. 1972, 46: 109 - 11
Hauser CR.Pruett RL.Mashburn TA. J. Org. Chem. 1961, 26: 1800 - 12
Dogan .Senol V.Zeytinci S.Koyuncu H.Bulut A. J. Organomet. Chem. 2005, 690: 430 - 13
Gras J.-L. Tetrahedron Lett. 1978, 19: 2955 - 14
Mehta G.Khan FA. J. Am. Chem. Soc. 1990, 112: 6140 - 15
Alonso F.Beletskaya IP.Yus M. Chem. Rev. 2002, 102: 4009 - 16
Khan FA.Prabhudas B. Tetrahedron Lett. 1999, 40: 9289 -
17a
Little WF.Reilley CN.Johnson JD.Lynn KN.Sanders AP. J. Am. Chem. Soc. 1964, 86: 1376 -
17b
Little WF.Reilley CN.Johnson JD.Sanders AP. J. Am. Chem. Soc. 1964, 86: 1382 -
17c
Mason JG.Rosenblum M. J. Am. Chem. Soc. 1960, 82: 4206 - 18
Perrin DD.Armarego WLF.Perrin DR. Purification of Laboratory Chemicals 2nd ed.: Pergamon Press; Oxford: 1980.