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1-[4- { 1,1′,1″,1‴-(1,3-Cyclopentadien-1,2,3,4-tetrayl)tetrakis} ]-(4,1-phenylen)-alkanone und deren Natrium-, Thallium(I)- und Fe(II)-Komplexe / 1-[4- { 1,1′,1″,1‴-(1,3-Cyclopentadiene-1,2,3,4-tetrayl)tetrakis} ](4,1 -phenylene)-alkanones and their Sodium, Thallium(I) and Iron(II) Complexes

1993; De Gruyter; Volume: 48; Issue: 3 Linguagem: Inglês

10.1515/znb-1993-0309

1865-7117

Herbert Schumann, Andreas Kucht, Homa Kucht, Alexander Lentz, Lothar Esser, Roman Weimann,

Ferrocene Chemistry and Applications

Tetraphenylcyclopentadiene (1) reacts with acylchlorides RC(O)Cl (R = CH 3 , C 3 H 7 , C 5 H 11 ,C 7 H 15 ) to form the corresponding [(cyclopentadiene tetrayl)tetrakis] (4,1-phenylene)alkanones C 5 H 2 (C 6 H 4 C(O)R-4) 4 (2a, 2b, 2c and 2d). 2a reacts with NaNH 2 generating the corresponding sodium salt Na[C 5 H(C 6 H 4 C(O)R-4) 4 ] (3a). 2a, 2b, 2c, and 2d react with T1OC 2 H 5 yielding the thallium(I) derivatives Tl[C 5 H(C 6 H 4 C(O)R-4) 4 ] (4a, 4b, 4c, 4d). Octaphenylferrocene (5) reacts with acylchlorides RC(O)Cl (R = CH 3 , C 3 H 7 , C 5 H 11 , C 7 H 15 ) to form octaacylated ferrocenes Fe[C 5 H(C 6 H 4 C(O)R-4) 4 ] 2 (6a, 6b, 6c and 6d). 6a can also be prepared by reacting FeI 2 with 3a. 6a reacts with NaOBr yielding Fe[C 5 H(C 6 H 4 C(O)OH-4) 4 ] 2 (7), which after reaction with C 5 H 11 OH and C 7 H 15 OH gives the corresponding octaesters Fe[C 5 H(C 6 H 4 C(O)OR-4) 4 ] 2 (8c and 8d). 6a and 6b are reduced by N 2 H 4 (H 2 O) to give Fe[C 5 H(C 6 H 4 CH 2 R-4) 4 ] 2 (11a and 11b). The X-ray crystal structures of tetraphenylcyclopentadiene (2 a), as well as of the partially and totally substituted ferrocene derivatives Fe[C 5 H(C 6 H 4 C(O)CH 3 -4) 4 ][C 5 H(C 6 H 4 C(O)CH 3 -4) 3 (C 6 H 5 )] (9), Fe[C 5 H(C 6 H 4 C(O)C 3 H 7 -4)(C 6 H 5 ) 3 ] 2 (10) and Fe[C 5 H(C 6 H 4 C 4 H 9 -4) 4 ] 2 (11b) have been determined. The 1 H and 13 C NMR spectra of the new compounds are reported and discussed.