Simple and Efficient Purification Protocol of 9-(Trifluoroacetyl)anthracene from Anthracene

REFERENCES

• Forbus Jr., T. R. ; Taylor , S. L. ; Martin , J. C. Reactions of the readily accessible electrophile, trifluoroacetyl triflate: A very reactive agent for trifluoroacetylations at oxygen, nitrogen, carbon, or halogen centers . J. Org. Chem. 1987 , 52 , 4156 – 4159 .
   Web of Science ®Google Scholar
• (a) Ben Hassine , B. ; Gorsane , M. ; Geerts-Evrard , F. ; Pecher , J. ; Martin , R. H. ; Castelet , D. Payne syntheses and enantioselective syntheses of epoxides from (E)-stilbene and α-methylstyrene . Bull. Soc. Chim. Belg. 1986 , 95 , 548 – 556 ; (b) Kiselvov , A. S. ; Harvey , R. G. Acylation of activated aromatic substrates under mild conditions with (RCO)2O/Me2S/BF3 . Tetrahedron Lett. 1995 , 36 , 4005 – 4008 .
   Google Scholar
• (a) Alder , K. ; Stein , G. ; von Budedenbrock , F. ; Eckardt , W. ; Frercks , W. ; Schneider , S. Steric course of addition and substitution reactions, I: Stereochemistry of the diene synthesis. Justus Liebigs Ann. Chem. 1934, 514, 1–33; (b) Diels , O. Mechanism of the diene synthesis, I: The course of the reaction between malonic ester, as well as cyanoacetic ester, and acetylenedicarboxylic ester in the presence of pyridine acetate. Dtsch. Chem. Ges. B 1942, 75, 1452–1467.
   Google Scholar
• Nicolaou , K. C. ; Snyder , S. A. ; Montagnon , T. ; Vassilikogiannakis , G. The Diels–Alder reaction in total synthesis . Angew. Chem. Int. Ed. 2002 , 41 , 1668 – 1698 .
   PubMed Web of Science ®Google Scholar
• Sankararaman , S. Pericyclic Reactions—A Textbook ; Wiley-VCH : Mörlenbach , 2005 .
   Google Scholar
• Backmann , W. E. ; Scott , L. B. The reaction of anthracene with maleic and fumaric acid and their derivatives and with citraconic anhydride and mesaconic acid . J. Am. Chem. Soc. 1948 , 70 , 1458 – 1461 .
   PubMed Web of Science ®Google Scholar
• (a) Sanhes , D. ; Favier , I. ; Saffon , N. ; Teuma , E. ; Gómez , M. Stereo-specific synthesis of hydroanthracene-dicarboximides . Tetrahedron Lett. 2008 , 49 , 6720 – 6723 ; (b) Goh , Y. W. ; White , J. M. Structure correlation study of some Diels–Alder cycloadducts of anthracene . Aust. J. Chem. 2009 , 62 , 419 – 424 .
   Web of Science ®Google Scholar
• Weber , E. ; Csöregh , I. ; Ahrendt , J. ; Finge , S. ; Czugler , M. Design of roof-shaped clathrate hosts: Inclusion properties and x-ray crystal structures of a free host and of inclusion compounds with 1-BuOH and DMF . J. Org. Chem. 1988 , 53 , 5831 – 5839 .
   Web of Science ®Google Scholar
• (a) Alder , K. ; Stein , G. ; Pries , P. ; Winckler , H. Syntheses in the hydroaromatic series, VI: Partially hydrogenated naphtho- and anthraquinones with hydrogen in the γ- and δ-position . Ber. Dtsch. Chem. Ges. 1929 , 62B , 2337 – 2372 ; (b) Diels , O. ; Thiele , W. E. Diene syntheses, XXX: The chloride of acetylenedicarboxylic acid . Chem. Ber. 1938 , 71B , 1173 – 1778 ; (c) Birney , D. ; Lim , T. K. ; Koh , J. H. P. ; Pool , B. R. ; White , J. M. Structural investigations into the retro-Diels–Alder reaction: Experimental and theoretical studies . J. Am. Chem. Soc. 2002 , 124 , 5091 – 5099 .
   Google Scholar
• Pirkle , W. H. ; Sikkenga , D. L. ; Pavlin , M. S. Nuclear magnetic resonance determination of enantiomeric composition and absolute configuration of γ–lactones using chiral 2,2,2-trifluoro-1-(9-anthryl)ethanol . J. Org. Chem. 1977 , 42 , 384 .
   Web of Science ®Google Scholar