The Chemistry of Acrylonitrile. II. Reactions with Ketones

Bruson, Herman Alexander; Riener, Thomas W.

doi:10.1021/ja01264a037

Cited by 56 publications

(21 citation statements)

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“…Compounds II and III were prepared as described in Ref. [7], IV and V as described in [8], VI as described in [3], and VII and VIII as described in [9].…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Mesomorphic Properties of 4,4'-Di-n-alkyl-bibicyclo[2.2.2]octanes

Reiffenrath

Schneider

1981

Zeitschrift Für Naturforschung A

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“…Compounds II and III were prepared as described in Ref. [7], IV and V as described in [8], VI as described in [3], and VII and VIII as described in [9].…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Mesomorphic Properties of 4,4'-Di-n-alkyl-bibicyclo[2.2.2]octanes

Reiffenrath

Schneider

1981

Zeitschrift Für Naturforschung A

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“…Cyclohexanone undergoes cyanoethylation easily to produce 2,2,6,6-tetrakis(2-cyanoethyl)cyclohexanone 5 [33] as it is shown in Scheme 2. cyclohexanone and acetone.…”

Section: Resultsmentioning

confidence: 99%

“…The compound 11 which can be considered the first generation dendrimer with cyano end groups has already been known from literature [33] though its structural data had to be complemented. It corresponded well to our measurements (NMR, MS, IR) anyway (Figure 4, Experimental).…”

Section: Resultsmentioning

confidence: 99%

Guanamine Dendrimerization

Maciejewski

Bednarek²,

Janiszewska

et al. 2000

Journal of Macromolecular Science, Part A

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A synthesis of dendrimers and hyperbranched polymers by using cycloaddition of cyanoguanidine to nitriles and cyanoethylation reaction is reported. Both reactions proceeded in the presence of a basic catalyst (alkaline hydroxides and Triton B, respectively). ORDER REPRINTSThe guanamine dendrimerization process has been carried out up to 4 th generations ended with cyano or amine groups. Intermediates and product substances, as well as by-products were identified by FT-IR, 1 H and 13 C NMR, MS, FIB-MS, and elemental analysis. Hyperbranched polymers were characterized by gel permeation choursomatography (GPC). Polyguanamine dendrimer (PGD) molecules exhibited expanded form in dimethylacetamide solution and low polydispersity (1.12-1.26). Observed contraction of the macromolecules was growing towards higher generations reaching an extreme at generation 4. The degree of branching of the products were within the range of 0.81-0.87 on the 0-1 scale.Decyanoethylation, hydrolysis, and intramolecular cyclization, as side reactions, were observed on the cycloaddition steps of dendrimerization. Some main stream dendrimerization products, i.e., tetrakis [2-(2,4-diamino-1,3,5-triazin-4-yl)ethyl]2,4-diamino-6-phenyl-1,3,5-triazine and 2,2,6,6-tetrakis[2-(2,4-diamino-1,3,5-triazin-6-yl)ethyl]cyclohexanone as well as by-products, i.e., 2,6,6-tris[2-(2,4-diamino-1,3,5-triazin-6-yl)ethyl] cyclohexanone, 2,6,6-tris(2-cyanoethyl)cyclohexanone and a dilactam have been isolated as new compounds. Spectral data for N 2 N 2 N 4 N 4 -tetrakis(2-cyanoethyl)-6-phenyl-1,3,5-triazine, 2,2,-6,6-tetrakis(2-cyanoethyl)cyclohexanone, 1,1,1-tris(2-cyanoethyl)propanone-2 and 1,1,1-tris[2-(2,4-diamino-1,3,5-triazin-6yl)ethyl]propanone-2 have been complemented. 754 MACIEJEWSKI ET AL.

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“…The double addition of acrylonitrile on 3-phenylpropan-2-one under basic conditions yielded, after recrystallisation, 3-acetyl-1,5-dicyano-3-phenylpentane (7). [21] Hydrolysis of the nitrile functions was performed under aqueous basic conditions to obtain the diacid 8 in 72 % yield. [21] The formation of the cyclohexanone ring was achieved by heating 8 in acetic anhydride to form a cyclic anhydride intermediate, which was further thermolyzed at 250 8C to yield the functionalized cyclohexanone 9 after distillation.…”

Section: Synthesis Of the Bicycloa C H T U N G T R E N N U N G [222mentioning

confidence: 99%

Synthesis of Molecular Motors Incorporating para‐Phenylene‐Conjugated or Bicyclo[2.2.2]octane‐Insulated Electroactive Groups

Vives

Gonzalez

Jaud

et al. 2007

Chemistry A European J

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The insulating role of the bicyclo[2.2.2]octane fragment has been theoretically evaluated by comparing the electronic coupling parameter (V(ab)) in 1,4-bis(ferrocenyl)benzene (1) and 1,4-bis(ferrocenyl)bicyclo[2.2.2]octane (2). The geometries were optimized by DFT and an extended Hückel calculation was performed to evaluate V(ab) by the dimer splitting method. The calculations showed a 12-fold decrease of the electronic coupling from 60 meV for 1 to 5 meV for 2. The second part describes the synthesis of two potential molecular motors with one incorporating the insulating bicyclo[2.2.2]octane fragment. These molecules are based on a ruthenium complex bearing a tripodal stator functionalized to be anchored onto surfaces. The ferrocenyl electroactive groups and the cyclopentadienyl (Cp) rotor are connected through a p-phenylene spacer (5) or through a spacer incorporating an insulating bicyclo[2.2.2]octane moiety (6).

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The Chemistry of Acrylonitrile. II. Reactions with Ketones

Cited by 56 publications

References 0 publications

Synthesis and Mesomorphic Properties of 4,4'-Di-n-alkyl-bibicyclo[2.2.2]octanes

Synthesis and Mesomorphic Properties of 4,4'-Di-n-alkyl-bibicyclo[2.2.2]octanes

Guanamine Dendrimerization

Synthesis of Molecular Motors Incorporating para‐Phenylene‐Conjugated or Bicyclo[2.2.2]octane‐Insulated Electroactive Groups

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