Selectivity versus reactivity: The safe, efficient metal hydride reduction of a bifunctional organic

Smith, Katrina; Beauvais, Robert; Holman, R. W.

doi:10.1021/ed070pa94

Cited by 7 publications

(7 citation statements)

References 2 publications

(2 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Tritium‐labelled 16:0 and 18:1n‐9 FA were converted to the corresponding FAlc by LiAlH 4 reduction as described by Smith et al. (1993).…”

Section: Methodsmentioning

confidence: 99%

Utilization and metabolism of palmityl and oleoyl fatty acids and alcohols in caecal enterocytes of Atlantic salmon (Salmo salar L.)

Bogevik¹,

Olsen²,

Tocher³

2008

Aquaculture Nutrition

View full text Add to dashboard Cite

The substitution of fish oil with wax ester-rich calanoid copepod-derived oil in diets for carnivorous fish, such as Atlantic salmon, has previously indicated a lower lipid digestibility.This suggests that the fatty alcohols (FAlc) present in wax esters may be a poorer substrate for intestinal enzymes than the fatty acids (FA) in triacylglycerol, the major lipid in fish oil. The hypothesis tested was that the possible lower utilization of dietary FAlc by salmon enterocytes is at the level of uptake and that subsequent intracellular metabolism was identical to that of FA. A dual-labelled FAlc-FA metabolism assay was employed to determine simultaneous FAlc and FA uptake and relative utilisation in enterocytes isolated from pyloric caeca of Atlantic salmon fed either a diet supplemented with fish oil or wax ester-rich FAlc and FA metabolism. Metabolic modification by elongation and/or desaturation was generally low at 1-5% of uptake. We conclude that our hypothesis was generally proved in that the uptake of FAlc by salmon enterocytes was lower than the uptake of FA and that subsequent intracellular metabolism of FAlc was similar to that of FA. However, unesterifiedFAlc was possibly recovered in the cells suggesting that the conversion to FA may not be concomitant with uptake.

show abstract

“…Tritium‐labelled 16:0 and 18:1n‐9 FA were converted to the corresponding FAlc by LiAlH 4 reduction as described by Smith et al. (1993).…”

Section: Methodsmentioning

confidence: 99%

Utilization and metabolism of palmityl and oleoyl fatty acids and alcohols in caecal enterocytes of Atlantic salmon (Salmo salar L.)

Bogevik¹,

Olsen²,

Tocher³

2008

Aquaculture Nutrition

View full text Add to dashboard Cite

show abstract

“…For catalytic hydrogenation of the oxo group of LA catalysed by ruthenium and rhodium complexes see Refs 223 and 224. More profound reduction of LA derivatives to diol or valeric acid is also possible. Thus reduction of LA with lithium aluminium hydride gives racemic pentane-1,4-diol, 225 while electrochemical reduction of LA under conditions of catholyte recirculation and membrane separation of anolyte gives valeric acid. 226 Bakers yeast reduce LA esters to 4-hydroxyvalerates in good yields and then to (R)-g-valerolactone and (S)-pentane-1,4diol.…”

Section: Oxidation and Reduction Reactionsmentioning

confidence: 99%

Levulinic acid in organic synthesis

1999

View full text Add to dashboard Cite

“…All the reactions must be carried out under the strict supervision of the instructor. Caution: LiAlH 4 powder, 21 in contact with water, releases flammable gases which may ignite spontaneously. Pd(C) may cause an allergic skin reaction.…”

Section: ■ Hazardsmentioning

confidence: 99%

Introduction to Covalent Organic Frameworks: An Advanced Organic Chemistry Experiment

et al. 2019

View full text Add to dashboard Cite

In order to introduce the concept of covalent organic frameworks (COFs), an important class of predictable crystalline porous polymers, an integrated laboratory experiment for advanced organic chemistry students is reported. The importance of these kind of polymers and their multiple applications are presented as a part of key concepts in polymer and organic chemistry, bridging these disciplines to materials science. Students carry out the synthesis and characterization of an iminelinked COF and its building blocks. The polymer is formed at room temperature by using solvent-assisted synthesis and mechanochemistry. Students are trained in solid state characterization techniques, including FTIR spectroscopy, thermogravimetric analysis (TGA), 13 C NMR crosspolarization−magic angle spinning (CP-MAS) NMR spectroscopy, and powder X-ray diffraction (PXRD), which are essential in the important field of reticular chemistry. Therefore, this lab experience constitutes a practical introduction to COFs.

show abstract

Selectivity versus reactivity: The safe, efficient metal hydride reduction of a bifunctional organic

Abstract: Microscale quantities allow students to perform otherwise dangerous observations of NaBH4 and LiAlH4 reductions.

Cited by 7 publications

References 2 publications

Utilization and metabolism of palmityl and oleoyl fatty acids and alcohols in caecal enterocytes of Atlantic salmon (Salmo salar L.)

Utilization and metabolism of palmityl and oleoyl fatty acids and alcohols in caecal enterocytes of Atlantic salmon (Salmo salar L.)

Levulinic acid in organic synthesis

Introduction to Covalent Organic Frameworks: An Advanced Organic Chemistry Experiment

Contact Info

Product

Resources

About