78704-75-3Relevant academic research and scientific papers
Convenient synthesis of chiral cyclophanes that can coordinate to metals
Sato, Masayuki,Uehara, Fumiaki,Sato, Kayo,Yamaguchi, Masahiko,Kabuto, Chizuko
, p. 8270 - 8276 (2007/10/03)
Optically pure cyclophanes possessing a 1,3-dicarbonyl moiety were conveniently synthesized from alkanedioyl dichloride in four steps. The intramolecular [4+2]cycloaddition of bis(acylketene)s generated by thermal decomposition of bis(4,6-dioxo-1,3-dioxane) proceeded smoothly, giving cyclophane pyranones in high yields. The compounds possessing 7-10 bridging methylenes were resolved by imine formation with (R)-1-phenylethylamine, followed by basic hydrolysis. These cyclophanes are optically active versions of acetylacetone or salicylaldehyde and formed complexes with metals such as copper and europium. X-ray analysis of the chiral copper complex indicated the pentacoordinated structure of the copper metal with syn configuration of the two bridging chains.
Synthesis and characterization of derivatized capped porhyrins
Tang, Hang,Wijesekera, Tilak P.,Dolphin, David
, p. 1366 - 1374 (2007/10/02)
The syntheses of porphyrins carrying either a fully hydrophobic cavity with a benzene moiety (32a,b) or a polar cavity with an amidobenzene (32c-d) are described.Terephthaldehyde (1) was converted to benzene-bisalkanoic acids (8, 10) and nitrobenzene-bisalkanoic acids (13 and 16) by using standard methods.The corresponding diacid chlorides 17a-d were used to acylate two equivalents of a β-unsubstituted pyrrole, and the ketonic groups were reduced by diborane.Following the transformation of the nitro function to the acetamide, appropriate modifications of the ethyl ester functions afforded the key bisformylpyrroles 25a-d.The cyanoacrylate-protected formyl pyrrole derivatives were monochlorinated at the α-methyl groups and condensed with two equivalents of an α-unsubstituted pyrrole to give the dipyrromethane dimers.Strong aqueous alkali caused saponification of the two ester groups and deprotection of the formyl functions to produce the dipyrromethane dimer 30, which, after thermal decarboxylation, was cyclized intramolecularly in acidic medium to give the porphyrins 32 (n = 4 or 5, X = H or NHCOCH3).
Synthesis of 6,21-Dioxo-5,22-diazaparacyclophane and Its Structural Characteristics
Kondo, Hiroki,Okamoto, Hiroshi,Kikuchi, Jun-ichi,Sunamoto, Junzo
, p. 3125 - 3128 (2007/10/02)
A novel paracyclophane, 6,21-dioxo-5,22-diazaparacyclophane (4) has been synthesized by a condensation of 5,5'-p-phenylenebis(valeroyl chloride) (5) with 4,4'-p-phenylenebis(butylamine) (3) by a high dilution method.It has been characterized by mea
