Premium
Action of Nucleophilic Reagents on Wool
Author(s) -
MIRÓ P.,
GARCÍADOMÍNGUEZ J. J.
Publication year - 1967
Publication title -
journal of the society of dyers and colourists
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.297
H-Index - 49
eISSN - 1478-4408
pISSN - 0037-9859
DOI - 10.1111/j.1478-4408.1967.tb02752.x
Subject(s) - lanthionine , chemistry , reagent , acetone , nucleophile , residue (chemistry) , pyridine , sulfur , organic chemistry , medicinal chemistry , amino acid , catalysis , biochemistry
Degradation of the disulphide bonds in wool caused by the action of nucleophilic reagents has been studied. The simultaneous formation of lanthionine and lysinoalanine on treatment with NaOH supports a mechanism entailing β‐elimination and the formation of an aminoacrylic acid residue as an intermediate. Treatment with KCN gives only lanthionine, thus excluding a β‐elimination mechanism; an S n 2 mechanism is suggested. The formation of lanthionine and lysinoalanine on treatment with Na 2 S rules out a simple S n 2 mechanism; it is suggested that a β‐elimination and an S n 2 mechanism operate simultaneously. The increase in the extent of reaction in the presence of organic solvents (acetone, ethanol, propanol, and pyridine) may be due to the breakage of hydrophobic bonds; this has been studied by using different acetone: water mixtures in the NaOH treatment.