Baker's yeast-mediated transformations of α-keto epoxides

Meth‐Cohn, Otto; Horák, Radim; Fouché, Gerda

doi:10.1039/p19940001517

Cited by 38 publications

(43 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The result of the original process of 1856-7 may still exist in three textile samples; the shawl shown on the right, corresponding to the analysed Science Museum F6 fabric, is one of these samples, see text. These data as well as the early data of Meth-Cohn and Smith [11] contradict Perkins claim that the definite formula for industrial mauveine was a C 27 , mauveine B or an isomer, and that the second colouring matter was pseudo-mauveine. As it will be shown in this work, mauveine is a complex mixture and the conclusions of both the modern authors and Perkin have their merits.…”

Section: Introductionmentioning

confidence: 68%

“…Although the research on the molecular structure of mauve began with Perkin himself, 5 it was resolved only in 1994, with the work of Meth-Cohn and Smith. [11] Other attempts to determine its structure were made during the end of the 19th century, [12,13] and in the 20th century. [14,15] In their pioneering analysis of historic salt samples, obtained from the Science Museum (London) and from the then Zeneca archives at Blackley (Manchester) published by Otto Meth-Cohn and Mandy Smith in 1994, two compounds were considered to be the main chromophores, mauveine A (major compound) and B, C 26 and C 27 structures, respectively, see Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

“…[14,15] In their pioneering analysis of historic salt samples, obtained from the Science Museum (London) and from the then Zeneca archives at Blackley (Manchester) published by Otto Meth-Cohn and Mandy Smith in 1994, two compounds were considered to be the main chromophores, mauveine A (major compound) and B, C 26 and C 27 structures, respectively, see Scheme 1. [11] Later on, by using a modern synthesis, some of us verified [16] that it was possible to obtain pseudo-mauveine (C 24 ), mono (C 25 ), di-(C 26 ), tri-(C 27 ) and tetramethylated (C 28 ) derivatives by using aniline, o-toluidine and p-toluidine as starting materials, and depending on the ortho to para ratios, to also obtain different isomeric ratios. Two other compounds, mauveine B2 and C, C 27 and C 28 compounds, respectively, were then discovered during analysis.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

A Study in Mauve: Unveiling Perkin's Dye in Historic Samples

Sousa

Melo

Parola

et al. 2008

Chemistry A European J

View full text Add to dashboard Cite

The analysis of different historic mauve samples—mauve salts and dyed textiles—was undertaken to establish the exact nature of the iconic dye produced by W. H. Perkin in the nineteenth century. Fourteen samples from important museum collections were analyzed, and it was determined that, in contrast to the general wisdom that mauveine consists of C26 and C27 structures, Perkin's mauveine is a complex mixture of at least thirteen methyl derivatives (C24 to C28) with a 7‐amino‐5‐phenyl‐3‐(phenylamino)phenazin‐5‐ium core. A fingerprint was established in which mauveines A or B were dominant, and in which mauveines B2 and C25 were found to be important tracers to probe the original synthesis. Counterion analysis showed that all the mauve salts should be dated after 1862. Perkin's original recipe could be identified in three textile samples, and in these cases, mauveines A and C25 were found to be the major chromophores. These are now shown to be the samples containing the “original mauve”.

show abstract

Section: Introductionmentioning

confidence: 68%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

A Study in Mauve: Unveiling Perkin's Dye in Historic Samples

Sousa

Melo

Parola

et al. 2008

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…[1][2][3][4] Many heterocycles are examples of pigment compounds. The design of pigment compounds has become easier with the development of computational chemistry; however, not all compounds can be designed theoretically since practical and experimental pigment compounds possess large molecules.…”

Section: Introductionmentioning

confidence: 99%

Development of Fluorescent 2-Pyrone Derivatives Using Ketene Dithioacetals for Organic EL Devices

Tominaga¹,

Mizuyama

Shigemitsu³

et al. 2009

HETEROCYCLES

View full text Add to dashboard Cite

-In recent years, organic electro luminescent (EL) materials have received considerable attention due to their potential application in next-generation display devices with high brightness levels, wide color ranges, and wide viewing angles. Fluorescent 2-pyrone derivatives have been synthesized using a convenient method involving ketene dithioacetals, which emit fluorescence (red, green, and blue) in both solution (dichloromethane and ethanol) and solid state. The structure-activity relationships of various 2-pyrone derivatives have been clarified.

show abstract

“…The two major components of Perkin's mauveine have been identified by NMR spectroscopy as mauveine A and mauveine B. 11,12 It is now known that over 12 homologues are present in mauveine. 13,14 The synthesis of mauveine by Perkin's method is low yielding and others have had difficulty repeating it.…”

mentioning

confidence: 99%

Synthetic Derivatives of Mauveine

Plater

Harrison

2013

Journal of Chemical Research

View full text Add to dashboard Cite

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 K 2 Cr 2 O 7 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 substituents are essential for the reaction to proceed. N-Methyl substituted chromophores were not demethylated in the reaction or by oxidation with K 2 Cr 2 O 7 in dilute H 2 SO 4 . N-Nitroso-bis(4-methylphenyl)amine rearranges smoothly to the orange compound, (2-nitro-4-methylphenyl)-4-methylphenylamine, when a solution in CH 2 Cl 2 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. Synthesis with bis(4-methylphenyl)amine (5)Since the four main components of mauveine (A, B, B 2 , C) 13 contain a key building block derived from p-toluidine (at Scheme 1 The synthesis of p-hydroxypseudo-mauveine 2. The numbering scheme of the phenazine ring is shown.

show abstract

Baker's yeast-mediated transformations of α-keto epoxides

Cited by 38 publications

References 24 publications

A Study in Mauve: Unveiling Perkin's Dye in Historic Samples

A Study in Mauve: Unveiling Perkin's Dye in Historic Samples

Development of Fluorescent 2-Pyrone Derivatives Using Ketene Dithioacetals for Organic EL Devices

Synthetic Derivatives of Mauveine

Contact Info

Product

Resources

About