Double Wittig reactions with 4-carboxybutylidene triphenylphosphorane as the key step in the synthesis of benzene derivatives metadisubstituted with ωω'-difunctionalized six-carbon chains

Provent, Christophe; Chautemps, Pierre; Gellon, Gisèle; Pierre, Jean‐Louis

doi:10.1016/0040-4039(96)00032-9

Cited by 6 publications

(13 citation statements)

References 8 publications

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“…A range of PA m PV polymers 3 have been prepared either (1) by polymerization of the O-substituted 5-hydroxyisophthaldehydes 2 or (2) by modifications of polymers bearing reactive groups at their C-5 positions. 5-Hydroxyisophthaldehyde ( 2a ) was synthesized (Scheme ) by employing a variation of a published procedure . Starting from the commercially available 5-hydroxydiethylisophthalate ( 4 ), reduction (LiAlH 4 /THF) gave (96%) 3,5-bishydroxymethylphenol ( 5 ) which was oxidized, on treatment with a Me 2 SO solution of potassium dichromate, to afford the key monomer 2a .…”

Section: Resultsmentioning

confidence: 99%

“…5-Hydroxyisophthaldehyde (2a) was synthesized (Scheme 3) by employing a variation of a published procedure. 10 Starting from the commercially available 5-hydroxydiethylisophthalate (4), reduction (LiAlH 4 /THF) gave (96%) 3,5-bishydroxymethylphenol (5) which was oxidized, on treatment with a Me 2 SO solution of potassium dichromate, 11 to afford the key monomer 2a. O-Alkylations of 2a could be performed (Scheme 4) under relatively mild conditions, i.e., K 2 CO 3 in DMF at room temperature using both bromides and iodides as the alkylating agents.…”

Section: Resultsmentioning

confidence: 99%

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Noncovalent Side-Wall Functionalization of Single-Walled Carbon Nanotubes

et al. 2003

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A family of poly[(m-phenylenevinylene)-co-(p-phenylenevinylene)]s, functionalized in the synthetically accessible C-5 position of the meta-disubstituted phenylene rings have been designed and synthesized: they are essentially poly{(5-alkoxy-m-phenylenevinylene)-co-[(2,5-dioctyloxy-p-phenylene)vinylene]} (PAmPV) derivatives. A range of these PAmPV polymers have been prepared both (1) by the polymerization of O-substituted 5-hydroxyisophthaldehydes and (2) by chemical modifications carried out on polymers bearing reactive groups at the C-5 positions. PAmPV polymers solubilize SWNT bundles in organic solvents by wrapping themselves around the nanotube bundles. PAmPV derivatives which bear tethers or rings form pseudorotaxanes with rings and threads, respectively. The formation of the polypseudorotaxanes has been investigated in solution by NMR and UV/vis spectroscopies, as well as on silicon oxide wafers in the presence of SWNTs by AFM and surface potential microscopy. Wrapping of these functionalized PAmPV polymers around SWNTs results in the grafting of pseudorotaxanes along the walls of the nanotubes in a periodic fashion. The results hold out the prospect of being able to construct arrays of molecular switches and actuators.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Noncovalent Side-Wall Functionalization of Single-Walled Carbon Nanotubes

et al. 2003

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“…Fractional crystallization then delivered pure quinaldine 44 11 (Scheme ). All aromatic aldehydes used are commercially available, with the exception of 46 , which was prepared in three steps from 5-hydroxyisophthalic acid 45 . Acetal 48 was elaborated through NaBH 4 reduction of commercially available terephthaldehyde mono(diethyl acetal) 47 (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Use of the Kohonen Neural Network for Rapid Screening of Ex Vivo Anti-HIV Activity of Styrylquinolines

et al. 2002

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Using the Kohonen neural network, the electrostatic potentials on the molecular surfaces of 14 styrylquinoline derivatives were drawn as comparative two-dimensional maps and compared with their known human immunodeficiency virus (HIV)-1 replication blocking potency in cells. A feature of the potential map was discovered to be related with the HIV-1 blocking activity and was used to unmask the activity of further five analogues, previously described but whose cytotoxicity precluded an estimation of their activity, and to predict the activity of 10 new compounds while the experimental data were unknown. The measurements performed later turned out to agree with the predictions.

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“…The diformyl compounds were prepared according to literature procedures [12,13]. Recrystallization from acetone solutions gave microcrystals of I and 2.…”

Section: Methodsmentioning

confidence: 99%

Benzoic acid and phenol derivatives of nitronyl nitroxide biradical as building blocks of organic molecule-based ferrimagnets

et al. 2000

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A crystal-engineering approach to organic ferrimagnets is reported. Coulombic energy between an anionic biradical with S = I and a cationic monoradical with S = 1/2 can be utilized as a driving force of cocrystallization of open-shell molecules with different spin quantum numbers, leading to organic salt ferrimagnets. In this study, 3,5-substituted phenol and benzoic acid derivatives of nitronyl nitroxide biradicals were synthesized as an ionizable S = 1 component of organic salt ferrimagnets. The molecular ground states of the biradicals in the neutral state were examined by continuous wave electron spin resonance (ESR) spectroscopy and static paramagnetic susceptibility measurements in the solid state. The molecular ground state of the phenol derivative was found to be triplet (S = 1) with the singlet-triplet energy gap of AE/k5 25 K, indicating that the biradical can be a building block of organic salt ferrimagnetics. The benzoic acid derivative was found to have a singlet (S = 0) ground state (4E/k5 ? -5 K), exemplifying that meta-(3,5)-linkage of unpaired electrons in it-aromatic rings does not necessarily give a triplet ground state for heteroatomic-substituted it conjugation. The molecular ground states of the biradicals determined in the ESR experiments were confirmed by the susceptibility in the solid state.

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Double Wittig reactions with 4-carboxybutylidene triphenylphosphorane as the key step in the synthesis of benzene derivatives metadisubstituted with ωω'-difunctionalized six-carbon chains

Cited by 6 publications

References 8 publications

Noncovalent Side-Wall Functionalization of Single-Walled Carbon Nanotubes

Noncovalent Side-Wall Functionalization of Single-Walled Carbon Nanotubes

Use of the Kohonen Neural Network for Rapid Screening of Ex Vivo Anti-HIV Activity of Styrylquinolines

Benzoic acid and phenol derivatives of nitronyl nitroxide biradical as building blocks of organic molecule-based ferrimagnets

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