Synthetic Analytical Studies on Organic Reagents for Biomaterials

Akiyama, Shuzo

doi:10.2116/analsci.10.365

ANAL. SCI.

1994

DOI: 10.2116/analsci.10.365

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Synthetic Analytical Studies on Organic Reagents for Biomaterials

Shuzo Akiyama

Abstract: "Synthetic analytical chemistry: Analytical chemistry with the aid of synthetic organic chemistry" is proposed by the present author as a new field of analytical chemistry. Such chemistry is developing on the basis of investigations of it-electron systems such as non-benzenoid aromatics (e.g. annulenes) or conjugated polyene and polyyne systems. Various kinds of organic reagents for analyses (ultraviolet/visible and near-infrared absorption, fluorescence, chemiluminescence and new silica gel column packings fo… Show more

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Cited by 5 publications

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Synthesis of a Remarkably Stable Dehydro[14]annulene

Palmer¹,

Parkin²,

Anthony³

2001

Angew. Chem.

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Dehydroannulenes are a fascinating class of carbon-rich molecules which have been studied intensively. [1] With the development of improved synthetic methodologies, these macrocycles are now being exploited for their potential material properties. Recent applications employ such annulenes as conjugated scaffolds for nonlinear optical applications [2] and as precursors for carbon nanotube synthesis. [3] We are currently exploring the use of fused dehydroannulenes as components in conjugated ladder polymers (e.g. acynes 1 and rylynes 2). R R R R R R n n acyne rylyne 1 2While the phenyldiacetylene macrocycles that comprise 1 are well-known compounds, [4] the class of dehydroannulenes that make up the backbone of 2 is poorly understood. The parent compound 3 was prepared in 1968 by Mitchell and Sondheimer, who were unable to fully characterize this new of the (R 1 /Et) 1,3-p interaction. The lower reactivity of dialkyl and alkyl aryl acrylonitriles compared to monosubstituted substrates is not unexpected considering the influence of the substituents on the electronic density at the double bond. This could also be responsible for the low reactivity of trisubstituted vinyl sulfoxide 8, but the (O/R 3 ) gauche and (Tol/R 3 ) gauche interactions present when R 3 =H can also be involved in the destabilization of both TS A and TS B .Desulfinylation of the amides 15 ± 17 and 19 with Raney nickel afforded the corresponding enantiopure amides 21 ± 24, which were isolated in good yields (b 70 %, Scheme 3). [21] In summary we have shown that the hydrocyanation of alkenyl sulfoxides with Et 2 AlCN takes place in a completely stereoselective manner. Taking into account the chemical versatility of the cyano and sulfinyl groups, this reaction can be considered as the key step in a short sequence that allows the creation of optically pure molecules containing tertiary or quaternary chiral centers from terminal alkynes, as illustrated with the preparation of amides 21 ± 24.

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Synthesis of a Remarkably Stable Dehydro[14]annulene

Palmer¹,

Parkin²,

Anthony³

2001

Angew. Chem.

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Synthesis of a Remarkably Stable Dehydro[14]annulene

Palmer

Parkin

Anthony

2001

Angew. Chem. Int. Ed.

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Sorption and preconcentration of metal ions on silica gel modified with 2,5-dimercapto-1,3,4-thiadiazole

Lessi

Filho

Moreira

et al. 1996

Analytica Chimica Acta

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Synthetic Analytical Studies on Organic Reagents for Biomaterials

Cited by 5 publications

References 47 publications

Synthesis of a Remarkably Stable Dehydro[14]annulene

Synthesis of a Remarkably Stable Dehydro[14]annulene

Synthesis of a Remarkably Stable Dehydro[14]annulene

Sorption and preconcentration of metal ions on silica gel modified with 2,5-dimercapto-1,3,4-thiadiazole

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