Synthesis 2013; 45(20): 2913-2918
DOI: 10.1055/s-0033-1339498
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Diarylated Aromatic Hydrocarbons by Dehydroxylation of Diols Using the Titanium(IV) Chloride and Triethylamine Reagent System

Mariappan Periasamy*
School of Chemistry, University of Hyderabad, Hyderabad 500046, A.P., India   Fax: +91(40)23012460   Email: mpsc@uohyd.ernet.in
,
Mallesh Beesu
School of Chemistry, University of Hyderabad, Hyderabad 500046, A.P., India   Fax: +91(40)23012460   Email: mpsc@uohyd.ernet.in
,
Masilamani Shanmugaraja
School of Chemistry, University of Hyderabad, Hyderabad 500046, A.P., India   Fax: +91(40)23012460   Email: mpsc@uohyd.ernet.in
› Author Affiliations
Further Information

Publication History

Received: 02 May 2013

Accepted after revision: 11 July 2013

Publication Date:
14 August 2013 (online)


Abstract

1,2-Diarylacenaphthylene, 9,10-diarylphenanthrene and 9,10-diarylanthracene derivatives were obtained in good yields (61–92%) in short reaction times (5–30 min) from the corresponding diols with the titanium(III) reagent prepared in situ using the TiCl4/Et3N reagent system in dichloromethane at 25 °C.

Supporting Information

 
  • References

  • 2 Gourdon A. Eur. J. Org. Chem. 1998; 2797
  • 4 Colwell WT, Brown V, Christie P, Lange J, Reece C, Yamamoto K, Henry DW. J. Med. Chem. 1972; 15: 771
  • 5 Banwell MG, Bezos A, Burns C, Kruszelnicki I, Parish CR, Su S, Sydnes MO. Bioorg. Med. Chem. Lett. 2006; 16: 181
  • 6 Cannon JG, Khonje PR, Long JP. J. Med. Chem. 1975; 18: 110
  • 7 Lewis FD, Burch EL. J. Phys. Chem. 1996; 100: 4055
  • 8 Lewis FD, Barancyk SV, Burch EL. J. Am. Chem. Soc. 1992; 114: 3866
  • 9 Machado AM, Munaro M, Martins TD, Davila LY. A, Giro R, Caldas MJ, Atvars TD. Z, Akcelrud LC. Macromolecules 2006; 39: 3398
  • 10 Liu R, Farinha JP. S, Winnik MA. Macromolecules 1999; 32: 3957
    • 11a Hercules DM. Acc. Chem. Res. 1969; 2: 301
    • 11b Hercules DM, Lansbury RC, Roe DK. J. Am. Chem. Soc. 1966; 88: 4578
  • 12 Natarajan P, Schmittel M. J. Org. Chem. 2012; 77: 8669
  • 13 Boyd TJ, Schrock RR. Macromolecules 1999; 32: 6608
  • 14 McMurry JE. Chem. Rev. 1989; 89: 1513
    • 15a Talukdar S, Banerji S. J. Org. Chem. 1998; 63: 3468 ; and references cited therein
    • 15b Dieguez HR, Lopez A, Domingo V, Arteaga JF, Dobado JA, Herrador MM, del Moral JF. Q, Barrero AF. J. Am. Chem. Soc. 2010; 132: 254
    • 16a Karunakar GV, Periasamy M. J. Org. Chem. 2006; 71: 7463
    • 16b Karunakar GV, Periasamy M. Tetrahedron Lett. 2006; 47: 3549
    • 16c Periasamy M, Jayakumar KN, Bharathi P. J. Org. Chem. 2005; 70: 5420
    • 16d Periasamy M. ARKIVOC 2002; (vii): 151
    • 16e Srinivas G, Periasamy M. Tetrahedron Lett. 2002; 43: 2785
    • 16f Periasamy M, Jayakumar KN, Bharathi P. Chem. Commun. 2001; 1728
    • 16g Periasamy M, Srinivas G, Karunakar GV, Bharathi P. Tetrahedron Lett. 1999; 40: 7577
    • 17a Hussaini SS, Raj AR. N, Huq CA. M. A. Tetrahedron Lett. 2007; 48: 775
    • 17b Moricnoni EJ, Connor WF. O, Kuhn LP, Keneally EA, Wallenberger FT. J. Am. Chem. Soc. 1959; 81: 6472
  • 18 The crystal data of compound 2f have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 911781. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk] or via www.ccdc.cam.ac.uk/data_request/cif. Unit cell parameters: a = 16.397(2) Å, b = 9.4410(13) Å, c = 26.943(4) Å, α = 90°, β = 94.170(2)°, γ = 90°, space group P21/c.
    • 19a Antler M, Laubengayer AW. J. Am. Chem. Soc. 1955; 77: 5250
    • 19b Fowles GW. A, Hoodless RA. J. Chem. Soc. 1963; 33
  • 20 He B, Tian H, Geng Y, Wang F, Müllen K. Org. Lett. 2008; 10: 773
  • 21 Das D, Engel E, Barbour LJ. Chem. Commun. 2010; 46: 1676
    • 22a Kurata H, Takehara Y, Kim S, Sakai K, Matsumoto K, Kawase T, Oda M. Synlett 2007; 2053
    • 22b Dyker G, Merz K, Oppl IM, Muth E. Synlett 2007; 897
    • 22c Brown JS, Sharp PR. Organometallics 2003; 22: 3604
    • 22d Dyker G. J. Org. Chem. 1993; 58: 234
    • 23a Liu Z, Larock RC. Angew. Chem. Int. Ed. 2007; 46: 2535
    • 23b Yoshikawa E, Yamamoto Y. Angew. Chem. Int. Ed. 2000; 39: 173
  • 24 Pena D, Perez D, Guitian E, Castedo L. J. Am. Chem. Soc. 1999; 121: 5827
  • 25 Kotha S, Ghosh AK, Deodhar KD. Synthesis 2004; 549