The Journal of Organic Chemistry 1976 Volume.41 No.13
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VOLUME 41 JUNE 25, 1 976 NUMBER 13 J OCE A h THE JOURNAL OF Organic Chemistry ch e m /c . PUBLISHED BIWEEKLY BY THE AMERICAN CHEMICAL SOCIETY t h e j o u r n a l o f Organic Chemistry EDITOR-IN-CHIEF: FREDERICK D. GREENE Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139 SENIOR EDITORS Werner Herz James A. Moore Martin A. Schwartz Florida State University University of Delaware Florida State University Tallahassee, Florida Newark, Delaware Tallahassee, Florida ASSISTANT EDITOR: Theodora W. Greene ADVISORY BOARD Robert A. Benkeser Neville Finch William M. Jones Albert I. Meyers Henry Rapoport John I. Brauman Paul G. Gassman Jay K. Kochi John G. Moffatt William Sheppard Orville L. Chapman Ralph Hirschmann James A. Marshall Roy A. Olofson Robert V. Stevens Stanton Ehrenson Donald M. Jerina James C. Martin Leo A. Paquette Barry M. Trost David A. Evans Carl R. Johnson Marvin L. Poutsma Nicholas J. Turro EX-OFFICIO MEMBERS: George H. 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Membership. & Subscription Services Editorial Department American Chemical Societv American.Ciiemical Society American Chemical Society 1155 16th St., N.W. P.O. Box 333? ' V : 20th and Northampton Sts. Washington, D.C. 20036 Colon,bus. Ohio 43210 . Easton, Pa. 18042 (202) 872-4600 ;e ii) 121-7230 (215)258-9111 N otice Authors last printed in the issue of January 9, 1976 JOCEAh 41(13) 2231-2354 (1976) ISSN 0022-3263 THE JOURNAL OF Organic Chemistry V o l u m e 4 1 , N u m b e r 13 J u n e 25,1976 Tadashi Sasaki,* Ken Kanematsu, 2231 Facile Seletal Rearrangement by Reaction of Polycyclic Olefins with Akihiro Kondo, and Kyoji Okada Lead(IV) and Thallium(III) Salts Philip E. Eaton,* Claudio Giordano, 2236 Annulated Cyclopentadienone Ketals. A Route to 1,2-Bridged and Ulrich Vogel Norbornenes Philip E. Eaton,* Claudio Giordano, 2238 cis,syn,cis-Tricyclo[6.3.0.03’7]undecane Ketones George Schloemer, and Ulrich Vogel Richard C. Larock 2241 Mercury in Organic Chemistry. 7. A Convenient Synthesis of Symmetrical Conjugated Dienes and Polyenes Brian F. Hegarty and 2247 Mercuration of Naphthalene— Salient Features William Kitching* Roger L. Clough, Pierre Mison, and 2252 Coupling of Nonequivalent Aromatic Rings by Soluble Nickel John D. Roberts* Catalysts. A General Route to the 1,8-Diarylnaphthalenes Thomas S. Croft* and John J. McBrady 2256 Reduction of Perfluoroacyl Halides with Organosilicon Hydrides. A Direct Synthesis of Fluorine Containing Esters and Lactones R. Weiss,* H. Kölbl, and C. Schlierf 2258 Controlled Substituent Exchange in Cyclopropenium Ions. Role of Counterion in Friedel-Crafts Reactions of the Trichlorocyclopropenium Ion Douglas E. Applequist* and 2262 Substituent Effects in the Homolytic Brominolysis of Substituted Lee F. McKenzie Phenylcyclopropanes Edwin D. Stevens,* James D. Kramer, 2266 X-Ray Crystal Structure Analysis of Triquinacene at 90 K and Leo A. Paquette ■ Masafumi Yoshimoto and 2269 Quantitative Structure-Activity Relationships of D- and Corwin Hansch* L-N-Acyl-a-aminoamide Ligands Binding to Chymotrypsin. On the Problem of Combined Treatment of Stereoisomers Alfred Hassner* and James E. Galle 2273 Ring Opening of Aziridine Phosphonates. Correlation of Structure, Nuclear Magnetic Resonance Spectra, and Reactivity S. Kukolja,* M. R. Gleissner, 2276 Synthesis of 3-Hydroxy-, 3-Chloro-, and 3-Methoxy-3-cephems from A. I. Ellis, D. E. Dorman, and Penicillins via 4-Dithio-2-azetidinone Intermediates J. W. Paschal Nobuyuki Ishibe* and Makoto Tamura 2279 Photochemical Reaction of 4-Diphenylmethylene-4H-thiopyrans Stephen R. Byrn,* 2283 Comparison of the Solid and Solution Conformations of Methapyriline, Constance Wier Gräber, and ■ Tripelennamine, Diphenhydramine, Histamine, and Choline. The Sharon L. Midland Infrared-X-Ray Method for Determination of Solution Conformations Yves Letourneux, Güniz Büjüktür, 2288 20-Methylcholesterol Maria T. Ryzlak, Ajit K. Benerjee, and Marcel Gut* Bhaskar R. Samant and 2292 Synthesis and Cyclization of 21-Hydroxyethylthioprogesterone Frederick Sweet* Derivatives William W. Lee,* Abelardo P. Martinez, 2296 Daunomycinone Analogues via the Diels-Alder Reaction. Synthesis Thomas H. Smith, and David W. Henry and Chemistry of Some 6,ll-Dihydroxy-5,12-naphthacenediones Sidney M. Hecht,* Benjamin L. Adams, 2303 Chemical Transformations of 7,9-Disubstituted Purines and Related and John W. Kozarich Hetercycles. Selective Reduction of Imines and Immonium Salts Jack E. Baldwin,* 2312 A Convenient Route to the Dihydroxyacetone Substituent O. William Lever, Jr., and Nathan R. Tzodikov B. Lee,* P. R. Story, and 2314 Macrocycles. Synthesis and Thermal Decomposition of J. R. Sanderson 3-Benzosuberone Diperoxide- 1 A * 9 «K1! 1)^1 rf4 ~ ' 2A J. Org. Chem., Voi. 41, No. 13,1976 Crown ethers, by virtue of NEWtheir unique ability CROWN to complex alkali metal cations, ETHERS have attained a place of /p-ominence LOWER in organic, inorganic PRICES and physical chemistry. They act as phase transfer catalysts transferring solid ionic reagents directly into organic solvents such as benzene or acetonitrile without the presence of water. Crown ethers have also proven useful in the selective extraction of certain ions from mixtures. They tend to be selective towards cations with radii near the size of the crown cavity. Polymers of dibenzo-crowns bind to cations more strongly than the free crowns. They have been used as column packings for the separation of alkali metal cations. We believe that they might also be used successfully to generate neuseable phase transfer catalyst beds. In addition to the new crowns we have also added some exotic mono- and di- methyl ethers of glycols.