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DOI: 10.1055/s-2005-861813
Heterosubstituted or Functionalized Derivatives of 1- and 2-(Trifluoromethyl)naphthalenes Emanating from Aryne Adducts
Publication History
Publication Date:
09 February 2005 (online)
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Abstract
More than two dozen new CF3-substituted naphthalene derivatives were prepared in an expedient way by employing 3- and 4-(trifluoromethyl)benzyne as the key intermediates. 2- and 4-Chlorobenzotrifluoride were treated with butyllithium and the organometallic species thus generated were allowed to decompose in the presence of furan. The resulting cycloadducts 1 and 14 were reduced to the (trifluoromethyl)naphthalenes 2 and 15, ring-opened to the (trifluoromethyl)naphthols 3, 16 and 17 and transformed to the dibromo adducts 5 and 18. The latter were stereoselectively converted into the bromo-1,4-epoxy-1,4-dihydro(trifluoromethyl)naphthalenes 6, 7, 19 and 20 and, by deoxygenation, into various bromo(trifluoromethyl)naphthalenes 8, 9, 21 and 22. Trifluoromethyl substituted naphthoic acids 10-13 and 23-26 were obtained when the bromo compounds 6-9 and 19-22 were subjected to a halogen/metal permutation followed by carboxylation.
Key words
arynes - halogen-metal permutation - metalation - naphthoic acids - trifluoromethyl groups
- 1
Leroux F.Jeschke P.Schlosser M. Chem. Rev. 2005, in press - 2
Schlosser M. Eur. J. Org. Chem. 2001, 3975 -
3a
Castagnetti E. Doctoral Dissertation Université Lausanne; Switzerland: 2001. p.24-38 -
3b
Castagnetti E. Doctoral Dissertation Université Lausanne; Switzerland: 2001. p.92-111 - 4
Bonnet-Delpon D.Charpentier-Morize M.Jacquot R. J. Org. Chem. 1988, 53: 759 - 5
Long Z.-Y.Duan J.-X.Lin Y.-B.Guo C.-Y.Chen Q.-Y. J. Fluorine Chem. 1996, 78: 177 - 6
Kuroboshi M.Hiyama T. Chem. Lett. 1992, 827 - 7
Urata H.Fuchikami T. Tetrahedron Lett. 1991, 32: 91 - 8
Le VP.Wells PR. Austr. J. Chem. 1992, 45: 1057 - 9
Heaney H. Chem. Rev. 1962, 62: 81 - 10
Pellissier H.Santelli M. Tetrahedron 2003, 59: 701 - 11
Wittig G.Pohmer L. Chem. Ber. 1956, 89: 1334 - 12
Gribble GW.Kelly WJ. Tetrahedron Lett. 1981, 22: 2475 - 13
Caster KC.Keck CG.Walls RD. J. Org. Chem. 2001, 66: 2932 - 14
Nakamura M.Oki M.Nakanishi H. Tetrahedron 1974, 30: 543 - 15
Brooke GM.Young AC. J. Fluorine Chem. 1976, 8: 223 - 16
Peña D.Pérez D.Guitián E.Castedo L. J. Org. Chem. 2000, 65: 6944 - 17
Tamborski C.Soloski EJ. J. Organomet. Chem. 1967, 10: 385 - 18
Harrison R.Heaney H. J. Chem. Soc. C 1968, 889 - 19
Coe PL.Pearl GM.Tatlow JC. J. Chem. Soc. C 1971, 604 - 20
Coe PL.Stephens R.Tatlow JC. J. Chem. Soc. 1962, 3227 - 21
Brewer JPN.Heaney H. Tetrahedron Lett. 1965, 6: 4709 - 22
Calander DD.Coe PL.Tatlow JC.Uff AJ. Tetrahedron 1969, 25: 25 - 23
Gribble GW.Easton NR.Eaton JT. Tetrahedron Lett. 1970, 11: 1075 - 24
Gribble GW.LeHoullier CS.Sibi M.Allen RW. J. Org. Chem. 1985, 50: 1611 - 25
Yamamoto G.Suzuki M.Oki M. Bull. Chem. Soc. Jpn. 1983, 56: 306 - 26
Bobbio C.Schlosser M. Eur. J. Org. Chem. 2001, 4533 - 27
Heiss C.Schlosser M. Eur. J. Org. Chem. 2003, 447 - 28
Schlosser M.Marull M. Eur. J. Org. Chem. 2003, 1569 - 29
Seiler P.Wurz J. Helv. Chim. Acta 1972, 55, 2693 - 30
Kunshenko BV.Alekseeva LA.Yagupolskii LM. Zh. Org. Khim. 1973, 9: 1954 ; Russ. J. Org. Chem. (Engl. Transl.) 1973, 9, 1971; Chem. Abstr. 1973, 79, 146278