Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2004(16): 2751-2759
DOI: 10.1055/s-2004-834872
DOI: 10.1055/s-2004-834872
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Cyclophanes. Part LII: [1] Ethynyl[2.2]paracyclophanes - New Building Blocks for Molecular Scaffolding
Further Information
Received
28 March 2004
Publication Date:
07 October 2004 (online)
Publication History
Publication Date:
07 October 2004 (online)
Abstract
The synthesis of seven ethynyl[2.2]paracyclophanes is described. The five diethynyl derivatives 4,5-diethynyl[2.2]paracyclophane (12), pseudo-gem- (13), pseudo-ortho- (14), pseudo-meta- (15), and pseudo-para-diethynyl[2.2]paracyclophane (16), the tetraethynyl compound 4,7,13,16-tetraethynyl[2.2]paracyclophane (17), and for comparison the mono-ethynylated hydrocarbon 4-ethynyl[2.2]paracyclophane (11) have been prepared. The structures of these new building blocks for carbon rich systems were determined by the usual analytical and spectroscopic methods.
Key words
ethynyl[2.2]paracyclophanes - oligoacetylenes - molecular scaffolding
- 1 For Part LI see:
El Shaieb K.Narayanan V.Hopf H.Dix I.Fischer A.Jones PG.Ernst L.Ibrom K. Eur. J. Org. Chem. 2003, 567 - 2
Carbon-Rich Compounds II, Topics in Current Chemistry
Vol. 201:
de Meijere A. Springer; Berlin: 1999. and references cited therein - For reviews see:
-
3a
Sondheimer F. Pure Appl. Chem. 1971, 28: 331 -
3b
Sondheimer F. Acc. Chem. Res. 1972, 5: 81 - 4
Rubin Y.Knobler CB.Diederich F. Angew. Chem., Int. Ed. Engl. 1991, 30: 698 ; Angew. Chem. 1991, 103, 708 - 5
Diercks R.Armstrong JD.Boese R.Vollhardt KPC. Angew. Chem., Int. Ed. Engl. 1986, 25: 268 ; Angew. Chem. 1986, 98, 270 - 6 For a summary see:
Hopf H. Classics in Hydrocarbon Chemistry Wiley-VCH; Weinheim: 2000. Chap. 15.2. p.457-472 - 7
Feldman KS.Kraebel CM.Parvez M. J. Am. Chem. Soc. 1993, 115: 3846-3847 - 8 For the preparation of several lower ethynylogs of 6 see:
Eaton PE.Galoppini E.Gilardi R. J. Am. Chem. Soc. 1994, 116: 7588 - 9
Naemura K.Hokura Y.Nakazaki M. Tetrahedron 1986, 42: 1763 - 10
Hopf H.Allmann R.Nagel M.El-Tamany S. Chem. Ber. 1982, 115: 3203 -
11a
Müller S.Liepold B.Roth GJ.Bestmann H.-J. Synlett 1996, 521 -
11b
Ohira S. Synth. Commun. 1989, 19: 561 -
12a
Rozenberg V.Kharitonov V.Antonov D.Sergeeva E.Aleshkin A.Ikonnikov N.Orlova S.Belokon’ Y. Angew. Chem., Int. Ed. Engl. 1994, 33: 91 ; Angew. Chem. 1994, 106, 106 -
12b
Hopf H.Barrett DG. Liebigs Ann. Chem. 1995, 449 - 13
Hopf H.Raulfs F.-W.Schomburg D. Tetrahedron 1986, 42: 1655 ; and references cited therein -
14a
Aly AA.Hopf H.Ernst L. Eur J. Org. Chem. 2000, 3021 -
14b
Zitt H.Dix I.Hopf H.Jones PG. Eur. J. Org. Chem. 2001, 2298 -
14c For a summary of the literature on this reaction see:
Hopf H. In Modern Cyclophane ChemistryGleiter R.Hopf H. Wiley-VCH; Weinheim: 2004. p.198 -
15a
Cram DJ.Truesdale EA. J. Org. Chem. 1980, 45: 3974 -
15b
Cram DJ.Hornby RB.Truesdale EA.Reich HJ.Delton MH.Cram JM. Tetrahedron 1974, 30: 1757 - 16
König B.Knieriem B.de Meijere A. Chem. Ber. 1993, 126: 1643 - 17
Boydston AJ.Bondarenko L.Dix I.Weakley TJ.Hopf H.Haley MM. Angew. Chem. Int. Ed. 2001, 40: 2986 ; Angew. Chem. 2001, 113, 3074 - 18
Savinsky R.Hopf H.Dix I.Jones PG. Eur. J. Org. Chem. 2001, 4595 - 19
Zitt H.Dix I.Hopf H.Jones PG. Eur. J. Org. Chem. 2001, 2298 -
20a
Callant P.D’Haenens L.Vandewalle M. Synth. Commun. 1984, 14: 155 -
20b
Colvin EW.Hamill BJ. J. Chem. Soc., Chem. Commun. 1973, 151 -
20c
Colvin EW.Hamill BJ. J. Chem. Soc., Perkin Trans. 1 1977, 869 - 21
Dix I. Ph.D. Dissertation Technical University Braunschweig; Germany: 2002. -
22a
Reich HJ.Cram DJ. J. Am. Chem. Soc. 1969, 91: 3527 -
22b
Braddock DC.MacGilp ID.Perry BG. J. Org. Chem. 2002, 67: 8679