Concave Reagents, 71) Concave Benzoic Acids

Based on m-terphenyl units, concave benzoic acids 11a and 12a were prepared via the 2,6-diarylbenzoic acid 7a. Bromination of 7a with NBS gave 9, and cyclization of 9 with dithiols 10 led to the bimacrocyclic concave acids 11a and 12a. Their relative acidities were determined by photometric titrations in ethanol, and the three-dimensional structure of 11a was determined by X-ray analysis.

[1]  U. Lüning,et al.  Concave reagents, 6. Can the structure of concave reagents determine selectivities? , 1990 .

[2]  H. Hart,et al.  Synthesis of two noninterconvertible conformers of a single host. Self-filled and vaulted cappedophanes , 1990 .

[3]  Michael Müller,et al.  Concave Reagents, 5 Bimacrocyclic 1,10‐Phenanthroline Cyclophanes , 1990 .

[4]  Julius Rebek.  Molekulare Erkennung mit konkaven Modellverbindungen , 1990 .

[5]  J. Rebek.  Molecular Recognition with Model Systems , 1990 .

[6]  K. Peters,et al.  Concave reagents, 3. Synthesis, basicity, and conformation of new concave pyridines , 1990 .

[7]  Michael Müller,et al.  Concave Reagents, 4 Protonation of Nitronate Anions via concave Pyridines. Stereoselective C‐Protonation versus Nef Reaction , 1990 .

[8]  Steven C. Zimmerman,et al.  A Rigid Molecular Tweezer with an Active Site Carboxylic Acid: An Exceptionally Efficient Receptor for Adenine in an Organic Solvent , 1989 .

[9]  Michael Müller,et al.  Concave Reagents. 2 Macrobicyclic 1,10‐Phenanthrolines , 1989 .

[10]  H. Hart,et al.  Cupped- and cappedophanes, two new general classes of compounds with molecular cavities , 1988 .

[11]  U. Lüning.  Concave Reagents: Syntheses of Macrobicyclic Pyridines , 1987 .

[12]  H. Hart,et al.  A one-pot synthesis of m-terphenyls, via a two-aryne sequence , 1986 .

[13]  T. Mcmorris,et al.  An efficient synthesis of pterosin C and other pterosins , 1984 .

[14]  M. Brink.  Eine verbesserte Synthese von [2.2] Paracyclophan und 4-Formyl-[2.2] paracyclophan , 1975 .

[15]  R. H. Mitchell,et al.  Transformation of sulfide linkages to carbon-carbon double bond. Syntheses of cis- and trans-15,16-dimethyldihydropyrene and trans-15,16-dihydropyrene , 1974 .

[16]  L. Radom,et al.  Internal rotation in some organic molecules containing methyl, amino, hydroxyl, and formyl groups , 1972 .

[17]  Hilton A. Smith,et al.  Physiologically Active Compounds. III. Hydrochlorides of Amino Esters of Phenylcyclohexylglycolic Acids, of Amides of Benzilic, Phenylcyclohexyl- and Dicyclohexylglycolic, and Phenylcyclohexylacetic Acids; 2-Methylthioethyl Ester Methiodides of Substituted Benzilic Acids , 1959 .

[18]  W. Wenner.  BIS(BROMOMETHYL) COMPOUNDS , 1952 .