1-[4-{1,1′,1″,1‴,1′′′′-(1,3-Cyclopentadien-1,2,3,4,5-pentayl)pentakis}]-(4,1-phenylen)-alkanone und -benzoesäure pentaalkylester und deren Natrium- und Thallium(I)-Komplexe / 1-[4-{1,1′,1″,1‴,1′′′′-( 1,3-Cyclopentadiene-1,2,3,4,5-pentayl)pentakis}]-(4,1-phenylene)-alkanones and -benzoic Acid Pentaalkyl Esters and their Sodium- and Thallium(I) Complexes

Abstract

Pentaphenylcyclopentadiene (1) reacts with acyl chlorides RC(O)Cl (R = CH3, C3H7, C5H11, C7H15) with formation of the corresponding [(cyclopentadiene pentayl)pentakis] (1,4-phenylene) alkanones C5H(C6H4C(O)R-4)5 (2a, 2c, 2d and 2e). 2 a reacts with KOCl in water/dioxane to yield C5Cl(C6H4C(O)OH-4)5 (3), which after reaction with C2H5OH and C5H11OH gives the pentaesters C5Cl(C6H4C(O)OR-4)5 (4b and 4d), and after reaction with (CH3)3SnH the corresponding [(cyclopentadiene pentayl)pentakis] benzoic acid pentaalkyl esters C5H(C6H4C(O)OR-4)5 (5b and 5d). Reaction of 2a, 2c, 2d, 2e and 5b with NaNH2 results in the formation of the sodium salts Na[C5(C6H4C(O)R-4)5] (6a, 6c, 6d and 6e) and Na[C5(C6H4C(O)OC2H5-4)5] (7). 2a, 2c, 2d, 2e, 5b and 5d react with TlOC2H5 to give the thallium(I) derivatives Tl[C5(C6H4C(O)R-4)5] (8a, 8c, 8d, 8e) and Tl[C5(C6H4C(O)OR-4)5] (9b and 9d). The 1H and 13C NMR spectra of the new compounds are reported and discussed.