Unexpected cleavage of C–S bond in the hydrazination of 2-((3,5-di-tert-butyl-4-hydroxybenzyl)thio) nicotinate: synthesis and mechanistic studies by kinetic and computational approaches

doi:10.1016/J.TET.2015.10.077

Paper

Unexpected cleavage of C–S bond in the hydrazination of 2-((3,5-di-tert-butyl-4-hydroxybenzyl)thio) nicotinate: synthesis and mechanistic studies by kinetic and computational approaches

Published Feb 18, 2016 · N. Nordin, A. Ariffin, M. N. Daud

Tetrahedron

Q3 SJR score

2

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

Abstract hidden due to publisher request; this does not indicate any issues with the research. Click the full text link above to read the abstract and view the original source.

Study Snapshot

Hydrazination of 2-((3,5-di-tert-butyl-4-hydroxybenzyl)thio) nicotinate in alcoholic solution led to unexpected C-S bond cleavage, producing 2-thioxo-1,2-dihydro-pyridine-3-car

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Unexpected cleavage of C–S bond in the hydrazination of 2-((3,5-di-tert-butyl-4-hydroxybenzyl)thio) nicotinate: synthesis and mechanistic studies by kinetic and computational approaches

References

Hydrolysis of the quinone methide of butylated hydroxytoluene in aqueous solutions.

BHT should be used with caution in pharmaceutical formulations containing drugs or excipients capable of acting as nucleophiles, as its hydrolysis can produce a highly reactive product that may impact impurity profiles.

Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities

Butylated hydroxytoluene analogues show promising multipotent antioxidant activities, with compound 5 showing promising inhibition of lipid peroxidation in egg yolk.

Methyl 2-[(3,5-di-tert-butyl-4-hydroxybenzyl)sulfanyl]pyridine-3-carboxylate n-hexane hemisolvate

The crystallized ester shows a symmetric unit with two independent molecules and a hexane molecule, revealing a –CH2–S– linkage between aromatic rings and a hydrogen bond between them.

2-Sulfanylidene-1,2-dihydropyridine-3-carbohydrazide

This compound exhibits a linear chain motif along the b axis, with the amino group acting as a hydrogen-bond donor to adjacent molecules.

Analysis of synthetic antioxidants and preservatives in edible vegetable oil by HPLC/TOF-MS

HPLC/TOF-MS is a suitable method for routine qualitative and quantitative analysis of synthetic antioxidants and preservatives in edible vegetable oils.

Citations

Sulfonium ylide formation and subsequent C S bond cleavage of aromatic isopropyl sulfide catalyzed by hemin in aqueous solvent

Hemin and Triton X-100 effectively catalyze the sulfonium ylide formation and C S bond cleavage of aromatic isopropyl sulfides, potentially benefiting organosulfur drug late stage functionalization.

Nickel-Catalyzed Regioselective Cleavage of C(sp(2))-S Bonds: Method for the Synthesis of Tri- and Tetrasubstituted Alkenes.

This study presents a highly regioselective method for the synthesis of (Z)-vinylic sulfides 3 and its use in the synthesis of various tri- and tetrasubstituted alkenes, useful for drug and natural product development.