The (meso-octaethylporphyrinogenato)zirconium(IV) species [(Et(8)N(4))Zr(thf)] (1) binds the acetophenone potassium enolate [PhCOCH(2)K] (2) in its ion-pair form, [(eta(5):eta(1):eta(1):eta(1)-Et(8)N(4))Zr{PhC(CH2)O}K(thf)(3)] (3), and thus drives the aldol condensation reaction with acetophenone. The resulting aldolate, which occurs in a metallacyclic form due to the solvation of potassium by a phenyl ring, remains eta(1) (O)-bonded to zirconium, [(eta(5):eta(1):eta(1):eta(1)-Et(8)N(4))Zr{PhC(CH2)OC(O)C(Me)Ph}K](n) (4).
Bifunctional Carriers of Alkali-Metal Enolates: the Use of Zirconium meso-Octaethylporphyrinogen in Aldol Condensation Reactions / G., Solari; E., Solari; C., Floriani; A., Chiesi Villa; Rizzoli, Corrado. - In: ORGANOMETALLICS. - ISSN 0276-7333. - 16:(1997), pp. 508-510. [10.1021/om9609325]
Bifunctional Carriers of Alkali-Metal Enolates: the Use of Zirconium meso-Octaethylporphyrinogen in Aldol Condensation Reactions
RIZZOLI, Corrado
1997-01-01
Abstract
The (meso-octaethylporphyrinogenato)zirconium(IV) species [(Et(8)N(4))Zr(thf)] (1) binds the acetophenone potassium enolate [PhCOCH(2)K] (2) in its ion-pair form, [(eta(5):eta(1):eta(1):eta(1)-Et(8)N(4))Zr{PhC(CH2)O}K(thf)(3)] (3), and thus drives the aldol condensation reaction with acetophenone. The resulting aldolate, which occurs in a metallacyclic form due to the solvation of potassium by a phenyl ring, remains eta(1) (O)-bonded to zirconium, [(eta(5):eta(1):eta(1):eta(1)-Et(8)N(4))Zr{PhC(CH2)OC(O)C(Me)Ph}K](n) (4).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
