1,2-Didehydro-3- and -4-(trifluoromethoxy)benzene: The “Aryne” Route to 1- and 2-(Trifluoromethoxy)naphthalenes
2001; Wiley; Volume: 2001; Issue: 21 Linguagem: Inglês
10.1002/1099-0690(200111)2001
ISSN1434-193X
AutoresManfred Schlosser, Eva Castagnetti,
Tópico(s)Chemical Reactions and Mechanisms
ResumoEuropean Journal of Organic ChemistryVolume 2001, Issue 21 p. 3991-3997 Full Paper 1,2-Didehydro-3- and -4-(trifluoromethoxy)benzene: The "Aryne" Route to 1- and 2-(Trifluoromethoxy)naphthalenes Manfred Schlosser, Manfred Schlosser Institut de Chimie organique de l'Université, Bâtiment de Chimie (BCh), 1015 Lausanne-Dorigny, Switzerland Fax: (internat.) + 41-21/692-3965Search for more papers by this authorEva Castagnetti, Eva Castagnetti Institut de Chimie organique de l'Université, Bâtiment de Chimie (BCh), 1015 Lausanne-Dorigny, Switzerland Fax: (internat.) + 41-21/692-3965Search for more papers by this author Manfred Schlosser, Manfred Schlosser Institut de Chimie organique de l'Université, Bâtiment de Chimie (BCh), 1015 Lausanne-Dorigny, Switzerland Fax: (internat.) + 41-21/692-3965Search for more papers by this authorEva Castagnetti, Eva Castagnetti Institut de Chimie organique de l'Université, Bâtiment de Chimie (BCh), 1015 Lausanne-Dorigny, Switzerland Fax: (internat.) + 41-21/692-3965Search for more papers by this author First published: 05 October 2001 https://doi.org/10.1002/1099-0690(200111)2001:21 3.0.CO;2-JCitations: 35Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract Upon treatment of 1-bromo-2-(trifluoromethoxy)benzene with lithium diisopropylamide (LIDA) at −100 °C, 3-bromo-2-(trifluoromethoxy)phenyllithium is generated. It can be trapped as such, but isomerizes to afford 2-bromo-6-(trifluoromethoxy)phenyllithium when the temperature is raised to −75 °C. The latter intermediate can be directly obtained from 1-bromo-3-(trifluoromethoxy)benzene. 1-Bromo-4-(trifluoromethoxy)benzene gives 5-bromo-2-(trifluoromethoxy)phenyllithium at −100 °C, but at −75 °C it slowly eliminates lithium bromide, thus setting free 1,2-dehydro-4-(trifluoromethoxy)benzene. In the same way, 1,2-dehydro-3-(trifluoromethoxy)benzene can be generated from 1-bromo-3-(trifluoromethoxy)benzene. Both "arynes" can be intercepted in situ with furan. The resulting [4+2] cycloadducts can be reduced with zinc powder, giving 1- and 2-(trifluoromethoxy)naphthalenes, they may be submitted to acid-catalyzed isomerization to produce trifluoromethoxy-1-naphthols, or they may be brominated to afford vic-dibromo derivatives. Base-promoted dehydrobromination of the latter compounds produces 2- or 3-bromo-1,4-epoxy-1,4-dihydro-5- or −6-(trifluoromethoxy)naphthalenes, which undergo regioselective ring-opening in acidic media and halogen/metal exchange when treated with butyllithium. References 1 E. Castagnetti , M. Schlosser , Eur. J. Org. Chem. 2001 , 691 −695 . 10.1002/1099-0690(200102)2001:4 3.0.CO;2-A CASWeb of Science®Google Scholar 2 F. Mongin , M. Schlosser , Tetrahedron Lett. 1997 , 37 , 1559 −1562 . 10.1016/S0040-4039(97)00131-7 Web of Science®Google Scholar 3 F. Mongin , A. Tognini , F. Cottet , M. Schlosser , Tetrahedron Lett. 1998 , 39 , 1749 . 10.1016/S0040-4039(98)00028-8 CASWeb of Science®Google Scholar 4 F. Mongin, E. Marzi, M. Schlosser, Eur. J. Org. Chem. 2001, in press. Google Scholar 5 R. Ruzziconi, S. Leconte, M. Schlosser, unpublished work (2001). Google Scholar 6 G. Wittig , L. Pohmer , Angew. Chem. 1955 , 67 , 348 −348 . 10.1002/ange.19550671306 CASWeb of Science®Google Scholar 7 J. P. Brewer , H. Heaney , Tetrahedron Lett. 1965 , 7 , 4709 −4712 . 10.1016/S0040-4039(01)84039-9 Google Scholar 8 D. D. Callander , P. L. Coe , J. C. Tatlow , J. Chem. Soc., Chem. Commun. 1966 , 143 −144 . CASWeb of Science®Google Scholar 9 H. Heaney , J. M. Jablonski , Tetrahedron Lett. 1966 , 8 , 4529 −4531 . 10.1016/S0040-4039(00)70071-2 Google Scholar 10 G. W. Gribbe , W. J. Kelly , Tetrahedron Lett. 1981 , 22 , 2475 −2478 . 10.1016/S0040-4039(01)92936-3 Web of Science®Google Scholar 11 G. Yamamoto , M. Suzuki , M. Oki , Bull. Chem. Soc. Jpn. 1983 , 56 , 306 −313 . 10.1246/bcsj.56.306 CASWeb of Science®Google Scholar 12 G. Gaviña , S. V. Luis , A. M. Costero , P. Gil , Tetrahedron 1986 , 42 , 155 −166 . 10.1016/S0040-4020(01)87413-5 CASWeb of Science®Google Scholar 13 G. W. Gribble , D. J. Keavy , E. R. Olson , I. D. Rae , A. Staffa , T. E. Herr , M. B. Ferraro , R. H. Contreras , Magn. Res. Chem. 1991 , 29 , 422 −432 . 10.1002/mrc.1260290504 CASWeb of Science®Google Scholar 14 P. L. Coe , A. J. Waring , T. D. Yarwood , J. Chem. Soc., Perkin Trans. 1 1995 , 2729 −2738 . 10.1039/p19950002729 CASWeb of Science®Google Scholar 15 A. Altundaş , A. Daştan , M. M. McKee , M. Balcı , Tetrahedron 2000 , 56 , 6115 −6120 . 10.1016/S0040-4020(00)00561-5 CASWeb of Science®Google Scholar 16 L. M. Stock , H. C. Brown , Adv. Phys. Org. Chem. 1963 , 1 , 35 −154 ; spec. pp. 74, 89 and 123. 10.1016/S0065-3160(08)60277-4 CASWeb of Science®Google Scholar 17 R. J. Blint , T. B. McMahon , J. L. Beauchamp , J. Am. Chem. Soc. 1974 , 96 , 1269 −1278 . 10.1021/ja00812a001 CASWeb of Science®Google Scholar 18 H. Volz , W. D. Mayer , Justus Liebigs Ann. Chem. 1975 , 835 −848 . 10.1002/jlac.197519750502 CASWeb of Science®Google Scholar 19 J. Burdon , D. W. Davies , G. del Conde , J. Chem. Soc., Perkin Trans. 2 1976 , 1193 −1195 . 10.1039/p29760001193 CASWeb of Science®Google Scholar 20 H. Volz , H. J. Streicher , Tetrahedron 1977 , 33 , 3133 −3135 . 10.1016/0040-4020(77)80460-2 CASWeb of Science®Google Scholar 21 M. H. Lien , A. C. Hopkinson , J. Phys. Chem. 1984 , 88 , 1513 −1517 . 10.1021/j150652a014 CASWeb of Science®Google Scholar 22 R. D. Chambers , M. Salisbury , G. Asey , G. Moggi , J. Chem. Soc., Chem. Commun. 1988 , 680 −681 . 10.1039/c39880000680 CASWeb of Science®Google Scholar 23 V. I. Bakhmutov , M. V. Galakhov , Russ. Chem. Rev. 1988 , 57 , 839 −851 . 10.1070/RC1988v057n09ABEH003394 Google Scholar 24 P. S. Martin , K. Yates , I. G. Csizmadia , Can. J. Chem. 1989 , 67 , 2188 −2195 . 10.1139/v89-339 CASWeb of Science®Google Scholar 25 D. A. Stams , T. D. Thomas , D. C. MacLaren , D. Ji , T. H. Morton , J. Am. Chem. Soc. 1990 , 112 , 1427 −1434 . 10.1021/ja00160a021 CASWeb of Science®Google Scholar 26 E. Uggerud , J. Chem. Soc., Perkin Trans. 2 1996 , 1915 −1920 . 10.1039/p29960001915 CASWeb of Science®Google Scholar 27 C. F. Rodriquez , D. K. Bohme , A. C. Hopkinson , J. Phys. Chem. 1996 , 100 , 2942 −2949 . 10.1021/jp951994w CASWeb of Science®Google Scholar 28 G. Frenking , S. Fau , C. M. Marchand , H. Grützmacher , J. Am. Chem. Soc. 1997 , 119 , 6648 −6655 . 10.1021/ja970335p CASWeb of Science®Google Scholar 29 Z.-j. Li , J. S. Francisco , J. Chem. Phys. 1999 , 110 , 817 −822 . 10.1063/1.478049 CASWeb of Science®Google Scholar 30 G. A. Olah, Y. K. Mo, in Carbonium Ions, Vol. 5 (Eds.: G. A. Olah, P. V. R. Schleyer), Wiley, New York, 1976, 2135−2262 (Chapter 36). Google Scholar 31 M. Schlosser , J. Porwisiak , F. Morgin , Tetrahedron 1998 , 54 , 895 −900 . 10.1016/S0040-4020(97)10335-0 CASWeb of Science®Google Scholar 32 Q. Wang , H.-x. Wei , M. Schlosser , Eur. J. Org. Chem. 1999 , 3263 −3268 . 10.1002/(SICI)1099-0690(199912)1999:12 3.0.CO;2-U Web of Science®Google Scholar Citing Literature Volume2001, Issue21November 2001Pages 3991-3997 ReferencesRelatedInformation
Referência(s)