Über Arsenderivate organischer Sulfide. I. Mitteilung: Sekundäre Phenyl‐(β‐alkyl‐sulfid)‐arsonsäuren des Typus  und deren Derivate

Scherlin, S. M.; Jakubowitsch, A. I.

doi:10.1002/prac.19331380103

J. Prakt. Chem.

1933

DOI: 10.1002/prac.19331380103

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Über Arsenderivate organischer Sulfide. I. Mitteilung: Sekundäre Phenyl‐(β‐alkyl‐sulfid)‐arsonsäuren des Typus und deren Derivate

S. M. Scherlin¹,

A. I. Jakubowitsch²

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Cited by 2 publications

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“…Among lower molecular weight sulfides, certain hydroxydialkyl sulfides, e.g., 2-(methylthio)ethanol, are miscible with water, and 2-(isoamylthio)ethanol has an agreeable odor and is partially soluble in water . Consequently, we decided to prepare and examine selected hydroxydialkyl sulfides for borane complexation with the objective of developing a borane carrier of low volatility, odorless or of very mild odor, and completely miscible with water.…”

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confidence: 99%

Molecular Addition Compounds. 18. Borane Adducts with Hydroxydialkyl Sulfide Borates for Hydroboration. New, Essentially Odorless, Water-Soluble Sulfide Borane Acceptors for Hydroboration

et al. 2001

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Hydroxydialkyl sulfides of general formula RS(CH2CH2)nH (R = Et, t-Bu, i-Am; n = 1-3) and thiodiethanol monomethyl ether (9) have been synthesized and used as borane carriers. The compounds 3 and 6 (R = Et, n = 2, 3), 7 (R = t-Bu, n = 3), and 9 are completely miscible with water and exhibit only very mild odor. The sulfides were transformed into the corresponding borates by treatment either with boric acid or with diborane. The borates complex 3 mol of borane per 1 mol of borate to give highly reactive, stable, liquid adducts, hydroborating 1-octene in 15 min at room temperature. The adducts derived from water soluble sulfides 3 and 9, selected for the hydroboration of more hindered olefins, reacted readily with (-)-beta-pinene, 1-methylcyclohexene, and 2,3-dimethyl-2-butene. The carrier borates liberated from the adducts during hydroboration are readily hydrolyzed to give 3 and 9, which can be washed off with water from trialkylboranes or oxidation products. Consequently, hydroxydialkyl sulfides 3 and 9 are the first completely water-soluble sulfide borane carriers that can be washed off in the workup of hydroboration products. The adducts derived from 3 and 9 are new, highly promising reagents suitable for large scale hydroborations and reductions.

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confidence: 99%

Molecular Addition Compounds. 18. Borane Adducts with Hydroxydialkyl Sulfide Borates for Hydroboration. New, Essentially Odorless, Water-Soluble Sulfide Borane Acceptors for Hydroboration

et al. 2001

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Preparation of S-Vinylsulfilimines

Yamamoto¹,

Kakimoto²,

Ôkawara³

1979

Bulletin of the Chemical Society of Japan

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For the preparation of S-vinylsulfilimines (1), mainly S-phenyl-N-tosyl-S-vinylsulfilimine, three routes were examined, viz., (A) the reaction of vinyl sulfide with chloramine T, (B) that of 2-haloethyl phenyl sulfide with chloramine T followed by dehydrohalogenation, and (C) that of 2-hydroxyethyl sulfide with chloramine T followed by acetylation of the hydroxyl group and deacetoxylation. Route A has disadvantages of troublesome preparation of vinyl sulfides and low yield. Route B gives the precursor sulfilimine to 1 in good yield only by use of anhydrous chloramine T. Route C gives the best results in view of starting material and yield.

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Über Arsenderivate organischer Sulfide. I. Mitteilung: Sekundäre Phenyl‐(β‐alkyl‐sulfid)‐arsonsäuren des Typus und deren Derivate

Cited by 2 publications

References 3 publications

Molecular Addition Compounds. 18. Borane Adducts with Hydroxydialkyl Sulfide Borates for Hydroboration. New, Essentially Odorless, Water-Soluble Sulfide Borane Acceptors for Hydroboration

Molecular Addition Compounds. 18. Borane Adducts with Hydroxydialkyl Sulfide Borates for Hydroboration. New, Essentially Odorless, Water-Soluble Sulfide Borane Acceptors for Hydroboration

Preparation of S-Vinylsulfilimines

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