Nuclear Methylation of Phenols. A New Synthesis of Intermediates in the Preparation of Antisterility Factors

Caldwell, William T.; Thompson, Thomas R.

doi:10.1021/ja01873a002

Cited by 38 publications

(11 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, hydroquinone treated with 3 equiv. each of dimethylamine and formaldehyde gave 2,5-dimethylhydroquinone not tri-(dimethylaminomethyl)-hydroquinone (21). Also, 5,7-bis(piperidinomethyl)-8-quinolinol could not be prepared by means of the Mannich reaction with 8-quinolinol under usual conditions, since only monosubstituted Mannich base (7-piperidinomethyl-8-quinolinol) was formed (16).…”

Section: Studies On Lignin Model Compoundsmentioning

confidence: 99%

Coupling P-31 NMR with the Mannich reaction for the quantitative analysis of lignin

Jiang¹,

Argyropoulos²

1998

Rev. Can. Chim.

View full text Add to dashboard Cite

The reactivity of lignin model compounds under Mannich conditions with piperidine and formaldehyde was studied. The piperidinomethyl group was confirmed to be introduced quantitatively at sterically unhindered positions ortho to a phenolic hydroxyl when the substrate was allowed to react under ambient conditions. The sequential application of the Mannich reaction followed by quantitative 31 P NMR on a variety of lignin samples allowed the amounts of various aromatic groups bearing free phenolic hydroxyls to be determined. More specifically, the technique allowed the quantification of para-hydroxyl phenols, catechols, guaiacols, and phenols bearing C 5 or C 6 substituents. The quantitative reliability of the technique was also examined with a series of dissolved kraft lignins, isolated at various degrees of delignification. The data were found to favourably compare to those obtained by permanganate oxidation.Résumé : On a étudié la réactivité de composés modèles de la lignine dans la réaction de Mannich avec de la pipéridine et du formaldéhyde. Il a été confirmé que, lorsque le substrat réagit dans des conditions ambiantes, le groupe pipéridinométhyle s'introduit quantitativement dans les positions stériquement non empêchées en ortho de l'hydroxyle phénolique. L'application séquentielle de la réaction de Mannich sur divers échantillons de lignine, suivie d'une étude quantitative RMN du 31 P, permet de déterminer les quantités de divers groupes aromatiques portant des hydroxyles phénoliques. D'une façon plus spécifique, la technique permet de quantifier les para-hydroxyphénols, les catéchols, les guaïacols et les phénols portant des substituants en C 5 et en C 6 . On a aussi évalué la fiabilité quantitative de la technique avec une série de lignines kraft dissoutes, isolées à divers degrés de délignification. On a trouvé que les données se comparent favorablement à celles obtenues par oxydation avec le permanganate.Mots clés : lignine, composés modèles de la lignine, réaction de Mannich, résonance magnétique nucléaire (RMN), phénols, phosphore, pipéridine, analyse quantitative. [Traduit par la rédaction]Can.

show abstract

Section: Studies On Lignin Model Compoundsmentioning

confidence: 99%

Coupling P-31 NMR with the Mannich reaction for the quantitative analysis of lignin

Jiang¹,

Argyropoulos²

1998

Rev. Can. Chim.

View full text Add to dashboard Cite

show abstract

“…The Mannich base 1 was synthesised by the literature method. 15 Melting points were measured on Electrothermal 9100 apparatus. Infrared spectra were measured on a Perkin-Elmer 1717 FT spectrometer.…”

Section: Methodsmentioning

confidence: 99%

“…-methyl]naphthalen-1-ol (5) was synthesised according to the method of Caldwell and Thompson. 15 The reaction of 6-bromo-1-naphthol (4) with dibenzylamine in the presence of formaldehyde at room temperature afforded the Mannich base 5 in 42 % yield (Scheme 1).…”

Section: -Bromo-2-[(n N-dibenzylamino)mentioning

confidence: 99%

The synthesis of some novel substituted benzochromene derivatives

Büyükkıdan¹,

Ceylan

2003

j. chem. res. (s)

View full text Add to dashboard Cite

show abstract

“…From each group one compound was taken and thus 12 adsorptive materials were selected for the preparation of the PCS array ( Table 1). The compound N-(2-hydroxylbenzyl)didecylamine was synthesized according to the method described in the literature [24] and identified by elemental analysis and IR spectrometry. Other compounds used were commercial A.R.…”

Section: Methodsmentioning

confidence: 99%

A perfume odour-sensing system using an array of piezoelectric crystal sensors with plasticized PVC coatings

Cao

Lin

Wang

et al. 1996

Analytical and Bioanalytical Chemistry

View full text Add to dashboard Cite

Using PVC polymer as membrane matrix and di-n-octylphenyl phosphate (DOPP) as plasticizer, a piezoelectric crystal sensor (PCS) array with 12 adsorptive materials selected from 68 compounds by cluster analysis has been constructed as a perfume odour-sensing system. The frequency shift data obtained from the sensor array responding to four commercial perfume odours are first autoscaled and then treated by principal component analysis. The experimental results show that the plasticized PVC membrane PCS array provides improved performance of pattern recognition compared with the single adsorptive coating PCS array. The frequency shift response characteristics of these sensors have been investigated experimentally. The proposed sensor array has also been applied to the classification of commercial spirituous liquor, wine and soft drink samples, as well as aliphatic alcohol homologues and isomers.

show abstract

Nuclear Methylation of Phenols. A New Synthesis of Intermediates in the Preparation of Antisterility Factors

Cited by 38 publications

References 0 publications

Coupling P-31 NMR with the Mannich reaction for the quantitative analysis of lignin

Coupling P-31 NMR with the Mannich reaction for the quantitative analysis of lignin

The synthesis of some novel substituted benzochromene derivatives

A perfume odour-sensing system using an array of piezoelectric crystal sensors with plasticized PVC coatings

Contact Info

Product

Resources

About