Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 427-434 |
| Number of pages | 8 |
| Journal | Journal of Chemical Research |
| Volume | 37 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - Jul 2013 |
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Keywords
- mauve
- mauveine
- montmorillonite
- N-methyl-p-toluidine
- n-phenyl-p-phenylediamine
- Perkin
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Synthetic derivatives of mauveine. / Plater, M. John; Harrison, William T. A.
In: Journal of Chemical Research, Vol. 37, No. 7, 07.2013, p. 427-434.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthetic derivatives of mauveine
AU - Plater, M. John
AU - Harrison, William T. A.
PY - 2013/7
Y1 - 2013/7
N2 - Oxidation of phenosafranin and an excess of aniline gave a novel hydroxylated derivative of pseudo-mauveine. N-Methyl-p-toluidine and bis(4-methylphenyl)amine are efficient building blocks for making mauveine-related chromophores. Their oxidation with K2Cr2O7 is believed to form nitrogen centred radicals which then couple with an aromatic amine by homolytic aromatic substitution of hydrogen. The N-methyl substituent and the p-methyl sub-stituents are essential for the reaction to proceed. N-Methyl substituted chromophores were not demethylated in the reaction or by oxidation with K2Cr2O7 in dilute H2SO4. N-Nitroso-bis(4-methylphenyl)amine rearranges smoothly to the orange compound, (2-nitro-4-methylphenyl)-4-methylphenylamine, when a solution in CH2Cl2 is treated with montmorillonite at room temperature for 24 h. 2,4-Dimethylaniline has been used to make a mauveine homologue. The colour of silk dyed with mauveine chromophores has been compared to the colour of silk dyed with authentic 1862 mauveine.
AB - Oxidation of phenosafranin and an excess of aniline gave a novel hydroxylated derivative of pseudo-mauveine. N-Methyl-p-toluidine and bis(4-methylphenyl)amine are efficient building blocks for making mauveine-related chromophores. Their oxidation with K2Cr2O7 is believed to form nitrogen centred radicals which then couple with an aromatic amine by homolytic aromatic substitution of hydrogen. The N-methyl substituent and the p-methyl sub-stituents are essential for the reaction to proceed. N-Methyl substituted chromophores were not demethylated in the reaction or by oxidation with K2Cr2O7 in dilute H2SO4. N-Nitroso-bis(4-methylphenyl)amine rearranges smoothly to the orange compound, (2-nitro-4-methylphenyl)-4-methylphenylamine, when a solution in CH2Cl2 is treated with montmorillonite at room temperature for 24 h. 2,4-Dimethylaniline has been used to make a mauveine homologue. The colour of silk dyed with mauveine chromophores has been compared to the colour of silk dyed with authentic 1862 mauveine.
KW - mauve
KW - mauveine
KW - montmorillonite
KW - N-methyl-p-toluidine
KW - n-phenyl-p-phenylediamine
KW - Perkin
U2 - 10.3184/174751913X13718370656320
DO - 10.3184/174751913X13718370656320
M3 - Article
VL - 37
SP - 427
EP - 434
JO - Journal of Chemical Research
JF - Journal of Chemical Research
SN - 0308-2342
IS - 7
ER -