II. Ueber einige Derivate des Mesitylens und die Verseifbarkeit aromatischer Säurenitrile

Küster, F. W.; Stallberg, A.

doi:10.1002/jlac.18942780205

Cited by 22 publications

(2 citation statements)

References 3 publications

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“…Unfortunately, the nitrile resisted all attempts to hydrolyze it with either acid or alkali under drastic conditions. A precedent for this behavior was found in the experience of Küster and Stallberg (12) who found it impossible to hydrolyze cyanomesitylene; they found, however, that the mono-or dinitro-cyanomesitylenes could be hydrolyzed without difficulty. Accordingly, XXV was nitrated to the hitherto unknown asymmetric cyanide musk (V), the odor of which seems to be slightly more intense than that of its symmetrical isomer.…”

mentioning

confidence: 96%

NITRO MUSKS. III.¹ ASYMMETRICAL MUSKS OF THE DINITRO-tert-BUTYL-m-XYLENE SERIES

Carpenter¹,

Easter²

1954

J. Org. Chem.

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confidence: 96%

NITRO MUSKS. III.¹ ASYMMETRICAL MUSKS OF THE DINITRO-tert-BUTYL-m-XYLENE SERIES

Carpenter¹,

Easter²

1954

J. Org. Chem.

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“…Alternatively, 29 was first converted to 2,4,6-trimethyl-3-nitrobenzeneacetonitrile (31) [40], which was substituted to give 32. The subsequent reduction of the nitrile group to the amine function by LiAlH 4 had to be modified: BH 3´T HF specifically reduced the nitrile group of 32 but not the NO 2 group [41].…”

mentioning

confidence: 99%

Mimicking the Reaction of Phenylalanine Ammonia Lyase by a Synthetic Model

Rettig¹,

Sigrist²,

Rétey³

2000

HCA

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Dedicated to Professor Albert Eschenmoser on the occasion of his 75th birthday Phenylalanine and histidine ammonia lyases (PAL and HAL) catalyze the reversible conversion of aamino acids to the corresponding acrylic acids by elimination of ammonia. The prosthetic group 3,5-dihydro-5-methylidene-4H-imidazol-4-one (MIO) at the active site of both enzymes supposedly undergoes an electrophilic attack at the aromatic nucleus in the first step of the mechanism of action. Since no chemical analogy existed for such an electrophile-assisted elimination, we synthesized model compounds, some portion of which mimicked the essentials of the substrate phenylalanine and another portion the electrophilic Michael acceptor in a sterically appropriate distance. The first model, (AE)-rel-(1R,2S,3S)-3-[1-methylidene-2-oxo-2-(pyrrolidin-1-yl)ethyl]-2-phenylcyclohexanamine (7) did not react under Friedel-Crafts conditions in the expected way (Scheme 2). The second model compound (AE)-2-rel-(1R,2S,3S)-3-(dimethylamino)-2-(3-methoxyphenyl)cyclohexyl]prop-2-enal (12) with a more nucleophilic methoxyphenyl and a more electrophilic a,b-unsaturated carbonyl moiety, underwent an intramolecular Friedel-Crafts-type substitution, but no elimination of the dimethylamino group (Scheme 4). The third model compound, (AE)-g-[(dimethylamino)methyl]-3-methoxy-2,4,6-trimethyl-a-methylidenebenzenebutanal (25) eliminated dimethylamine upon treatment with Lewis acids and subsequent hydrolysis of the intermediate (Scheme 6). When the 3-methoxy-2,4,6-trimethylphenyl moiety of 25 was replaced by the 2,4,6-trimethyl-3-nitrophenyl group, no elimination product could be observed (Scheme 7).

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