The Stereology Concept: Novel Acidic Complexones and their Selectivity towards Cations

Leppkes, R.; Vögtle, Fritz

doi:10.1002/anie.198103961

Angew. Chem. Int. Ed. Engl.

1981

DOI: 10.1002/anie.198103961

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The Stereology Concept: Novel Acidic Complexones and their Selectivity towards Cations

R. Leppkes

Fritz Vögtle

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1982

1999

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Cited by 18 publications

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“…The binding properties of EDTA analogues bearing an o -quaterphenyl central unit towards metal ions were determined by Všgtle. 2 Cram studied transacylase mimics based upon the quaterphenyl system. 3 It was also found that o -quaterphenyl derivatives are involved in carbonÐcarbon bond activation processes catalyzed by Ni, Pd and Pt complexes.…”

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confidence: 99%

Efficient Synthesis of Octaalkyloxy-o-quaterphenyls via Base-Induced Biaryl Coupling

Schulte¹

1999

Synthesis

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Octamethoxy-o -quaterphenyl (8a) was prepared in three steps from 4-bromo-1,2-dimethoxybenzene (5a) employing two base-mediated biaryl couplings. Demethylation of 8a followed by alkylation with decyl bromide gave the tetradecyloxy-o -quaterphenyl (8c) .Interest in o -quaterphenyls 1 has been stimulated by different research areas (Scheme 1). Všgtle for example used bridged, helical o -quaterphenyls (quaterphenylophanes) to study the dependence of the UV absorption from the twisting of the aryl rings. 1 o -Quaterphenyls were also employed in host-guest chemistry. The binding properties of EDTA analogues bearing an o -quaterphenyl central unit towards metal ions were determined by Všgtle. 2 Cram studied transacylase mimics based upon the quaterphenyl system. 3 It was also found that o -quaterphenyl derivatives are involved in carbonÐcarbon bond activation processes catalyzed by Ni, Pd and Pt complexes. 4,5 The synthesis of these quaterphenyls relies mainly on the classical Ullmann reaction. 1,6 In addition Pd-catalyzed Suzuki coupling of aryl boronates, 7 Ni-catalyzed Kumada coupling of aryl Grignard reagents, 8 Cu(II)-catalyzed rearrangements of bora-aromatics, 5a oxidative coupling of metal phenolates, 9 and oxidative addition of Ni(0) complexes to biphenylene were used as well. 4b We have recently found that 3,3',4,4'-tetramethoxybiphenyl 6a (R = Me) could be prepared in 79% yield by treatment of 4-bromo-1,2-dimethoxybenzene 5a with 0.5 equivalents of butyllithium in THF at Ð78¡C (Scheme 2). 10,11 The formation of 6a had been observed previously during bromine-lithium exchange in 5a with butyllithum. 12d We anticipated that this clean biaryl formation, which does not require the use of expensive or toxic coupling agents 12 might be useful for the synthesis of o -quaterphenyl derivatives 1 as outlined in Scheme 1. We were particularly interested in o -quaterphenyls 1 with long alkyl or alkoxy chains as potential new liquid crystals. The results towards this end are reported below. A preliminary study revealed the scope and limitations of the base-induced biaryl coupling. Whereas most aryl bromides, like 4-bromobenzene, 1-bromonaphthaline, 4-bromo-N,N' -dimethylaniline, 1-bromo-4-nitrobenzene, 4-bromoanisole, and 1-bromo-2,4-dimethoxybenzene either did not react in the presence of 0.5 equivalents of butyllithium in THF or gave the butylated products, 13 only 4-bromo-1,2-didecyloxybenzene 5b and 2-bromoanisole (5c) gave the corresponding biphenyls 6b in 37% and 6c in 19% yield, respectively (Scheme 2). Although compounds 6b , c were obtained in lower yields as compared to 6a , the tetradecyloxy derivative 6b in particular is worth mentioning, because it is an important precursor for the synthesis of discotic liquid crystals bearing the triphenylene moiety. 14,15

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confidence: 99%

Efficient Synthesis of Octaalkyloxy-o-quaterphenyls via Base-Induced Biaryl Coupling

Schulte¹

1999

Synthesis

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Molekulare Pinzetten mit Kohlenwasserstoffgerüst und konvergenten Carboxygruppen

Güther¹,

Nieger

Vögtle³

1993

Angewandte Chemie

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Neuartige blautransparente Frequenzverdoppler auf der Basis von 1,8‐Di(hetero)aryl‐naphthalinen

Bahl¹,

Grahn²,

Reisner³

et al. 1995

Angewandte Chemie

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Durch konsekutive Suzuki‐Kupplungen sind aus der Boronsäure 1 1,8‐Diarylnaphthaline wie 2 (A = Acceptor, D = Donor) allgemein zugänglich. Aufgrund nichtkovalenter π‐π‐Wechselwirkungen sind diese deutlich NLO‐aktiver als ihre längerwellig absorbierenden 1,5‐Isomere und damit hochinteressante Alternativen zu den besten klassischen blautransparenten Frequenzverdopplern. magnified image

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The Stereology Concept: Novel Acidic Complexones and their Selectivity towards Cations

Cited by 18 publications

References 14 publications

Efficient Synthesis of Octaalkyloxy-o-quaterphenyls via Base-Induced Biaryl Coupling

Efficient Synthesis of Octaalkyloxy-o-quaterphenyls via Base-Induced Biaryl Coupling

Molekulare Pinzetten mit Kohlenwasserstoffgerüst und konvergenten Carboxygruppen

Neuartige blautransparente Frequenzverdoppler auf der Basis von 1,8‐Di(hetero)aryl‐naphthalinen

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