Stereochemical Effects on <i>N</i>-Nitrosamine Chemistry

Lyle, Robert; Fribush, Howard M.; Singh, Sunil P.; Saavedra, Jose E.; Lyle, Gloria G.; W, Barton R; Yoder, S.; Jacobson, Martin

doi:10.1021/bk-1979-0101.ch003

ACS Symposium Series

1979

DOI: 10.1021/bk-1979-0101.ch003

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Stereochemical Effects on N-Nitrosamine Chemistry

Robert Lyle

Howard M. Fribush

Sunil P. Singh

et al.

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1980

1983

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“…Emodin occurs widely in nature,2® and various procedures have been reported for its isolation, but all require prior collection of plant materials.7 We now describe a simple procedure for the isolation of emodin from readily avail-able8 Indian rhubarb root extract. The process also provides abundant quantities of chrysophanol (3).2b (1) Undergraduate Research Participant.…”

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confidence: 99%

Practical procedure for the isolation of emodin and chrysophanol

Kelly¹,

Chandrakumar²,

WALTERS³

et al. 1983

J. Org. Chem.

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Preparation of Trimethylsilyl Enol Ether 4. Triethylamine (377 mL, 2.7 mol) was added to a solution of isobutyraldehyde (180 mL, 2 mol) and chlorotrimethylsilane (372 mL, 2.6 mol) in dimethylformamide (650 mL). The mixture was refluxed at 95 °C for 20 h. After filtration, the solid was washed with pentane. The combined organic solution (2.5 L) was washed with saturated sodium bicarbonate solution (4X2 L). The organic layer was dried and fractionally distilled to give 178 g (61.5%) trimethylsilyl enol ether 4, bp 108-120 °C.Preparation of 3-(Phenylthio)-2,2-dimethylpropanal (12). To a solution of trimethylsilyl enol ether 4 (30 g, 20.8 mmol) and chloromethyl phenyl sulfide (11; 30 g, 18.9 mmol) in dry dichloromethane (200 mL) was added anhydrous zinc bromide (500 mg). After being stirred for 30 min, the solution was poured into an ice cold sodium chloride solution (500 mL) and extracted once more with dichloromethane (200 mL). The organic layer was dried over magnesium sulfate. Evaporation to dryness and distillation gave 12: 33 g (82%); bp 115 °C (1.7 mm).

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confidence: 99%

Practical procedure for the isolation of emodin and chrysophanol

Kelly¹,

Chandrakumar²,

WALTERS³

et al. 1983

J. Org. Chem.

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α-D-Glucuronide von 1-(N-Alkyl-N-nitrosoamino)-alkylalkoholen

Braun

Wießler

1980

Angew. Chem.

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α‐D‐Glucuronides of 1‐(N‐Alkyl‐N‐nitrosoamino)alkyl Alcohols

Braun

Wießler

1980

Angew. Chem. Int. Ed. Engl.

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Stereochemical Effects on N-Nitrosamine Chemistry

Cited by 5 publications

References 0 publications

Practical procedure for the isolation of emodin and chrysophanol

Practical procedure for the isolation of emodin and chrysophanol

α-D-Glucuronide von 1-(N-Alkyl-N-nitrosoamino)-alkylalkoholen

α‐D‐Glucuronides of 1‐(N‐Alkyl‐N‐nitrosoamino)alkyl Alcohols

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