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Titolo:
Synthesis of controlled pi-extended conjugate nanostructures of 1,1 '-ferrocene
Autore:
Rodriguez, JG; Pleite, S;
Indirizzi:
Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, SpainUniv Autonoma Madrid Madrid Spain E-28049 m Organ, E-28049 Madrid, Spain
Titolo Testata:
JOURNAL OF ORGANOMETALLIC CHEMISTRY
, volume: 637, anno: 2001,
pagine: 230 - 239
SICI:
0022-328X(200112)637:<230:SOCPCN>2.0.ZU;2-O
Fonte:
ISI
Lingua:
ENG
Soggetto:
NONLINEAR-OPTICAL-PROPERTIES; CRYSTAL-STRUCTURE; HYPERPOLARIZABILITIES; ETHYNYLFERROCENE; FERROCENYL;
Keywords:
ferrocenes; acetylenes; diynes; (E)- and (Z)-isomers; acetal; biphenyl; coupling reactions;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
24
Recensione:
Indirizzi per estratti:
Indirizzo: Rodriguez, JG Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, C1, E-28049 Madrid, Spain Univ Autonoma Madrid C1 Madrid Spain E-28049 Madrid, Spain
Citazione:
J.G. Rodriguez e S. Pleite, "Synthesis of controlled pi-extended conjugate nanostructures of 1,1 '-ferrocene", J ORGMET CH, 637, 2001, pp. 230-239

Abstract

Synthesis of the (EE)-1,1'-ferrocene nanostructures having controlled pi -extended conjugation was satisfactory carried out starting of 1-[2-(1,3-dioxolan)]-1-formylferrocene (1). The molecular unit (E)-1'-[2-(1,3-dioxolan)]-1-[beta-(p-iodophenyl)ethenyl]ferrocene (2), was obtained in excellent yield by treatment of I with p-iodobenzyl triphenylphosphonium ylid followed by Z -->E isomerization, catalyzed by iodine, in quantitative yield. Compound (E)-2 was transformed in (E)-1'-(2-(1,3-dioxolan)-1-[beta [4-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-ethenyl}ferrocene, (E)-4, by palladium catalyzed cross-coupling with 2-methyl-but-3-yn-2-ol. (E)-4 gives (E)-1-[beta-(4-ethynylphenyl)-ethenyl]-1'-[2-(1,3-dioxolan)]ferrocene (E)-5 by powder sodiumhydroxide treatment. The molecular unit (EE)-1-{beta-[4-(beta-(1'-formylferrocenyl)-ethenyl)-phenylethynyl]-phenyl]-ethenyl)-1'-formylferrocene, (E,E)-6, was synthesized by palladium catalyzed cross-coupling between the p-iodophenyl derivative (E)-2 and their ethynyl derivative (E)-5, in good yield. The (EE)-1,1'-(p-iodophenyl)ethenyl ferrocene, (EE)-7, was synthesized byreaction between 1,1'-diformylferrocene and the p-iodobenzyltriphenylphosphonium ylid, as a mixture of isomers which were purely isolated. Moreover, isomerization of the ZZ and E,Z mixture to the EE isomer, was induced by sunlight exposure, catalyzed by iodine, in quantitative yield. The (EE)-1,1'-[beta-(4-ethynylphenyl)-ethenyl]ferrocene, (EE)-10, was synthesized in goodyield, by palladium catalyzed cross-coupling of compound (EE)-7 with 2-methyl-but-3-yn-2-ol, followed by powder sodium hydroxide treatment. (C) 2001 Elsevier Science B.V. All rights reserved.

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Documento generato il 04/07/20 alle ore 17:35:00