Factors in the formation of isomerically and optically pure alkyl halides. Part X. Reactions of saturated aliphatic alcohols with thionyl chloride

Hudson, H. R.; Spinoza, G.Riga De

doi:10.1039/p19760000104

Cited by 29 publications

(14 citation statements)

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“…Surprinsingly, no trace of cis-7 was observed by analysis of the spectrum of the crude reaction products (entries 1 and 2) [16]. The method of Hudson, which uses thionyl chloride in HMPT, also gave bad results with a complex mixture of largely unidentified compounds [17]. Due to all these unfavourable features, this synthetic scheme had to be discontinued.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1,2-Diamino-1-phenylpropane Diastereoisomers from u-N-Trifluoroacetyl-2-amino-1-phenylpropan-1-ol

Dufrasne

Nève

2005

Monatshefte für Chemie

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Section: Resultsmentioning

confidence: 99%

Synthesis of 1,2-Diamino-1-phenylpropane Diastereoisomers from u-N-Trifluoroacetyl-2-amino-1-phenylpropan-1-ol

Dufrasne

Nève

2005

Monatshefte für Chemie

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“…2,4‐DCP was synthesized via a published method for converting secondary alcohols into the corresponding chlorides . Details are available elsewhere .…”

Section: Methodsmentioning

confidence: 99%

“…Reduction of the ketones was carried out with sodium borohydride in aqueous ethanol at ca. 10–25°C to afford alcohols that were used for the next step without further purification, following the published method for chloride synthesis referenced above and detailed in reference .…”

Section: Methodsmentioning

confidence: 99%

Chlorination of poly(vinyl chloride) model compounds in radical‐complexing solvents

Starnes

2015

Vinyl Additive Technology

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A potential route to the preparation of poly(1,2‐dichloroethylene) by the selective chlorination of poly(vinyl chloride) (PVC) was explored. During free‐radical chlorinations with Cl2, certain solvents play the very important role of forming complexes with the free chlorine atom that lead to changes in the pattern of chlorine substitution. In our work, the photochlorination of three model compounds for PVC, namely, 2,4‐dichloropentane, 3‐chloropentane, and 4‐chloroheptane, was carried out with molecular chlorine in the absence or presence of complexing solvents. The effects of these solvents on the chlorination selectivity were determined. During the conventional chlorination of sec‐alkyl chlorides with molecular chlorine, bridged‐radical intermediates are believed to be involved. They lead to vicinal dichlorides as the major products. However, we found that complexing solvents significantly increased the yields of geminal dichlorides instead. Such solvents also are well known to decrease reactivity in free‐radical chlorinations with Cl2. Thus, for both of these reasons, the chlorination of PVC with Cl2 in complexing solvents is unlikely to be useful for the preparation of poly(1,2‐dichloroethylene). J. VINYL ADDIT. TECHNOL., 22:405–409, 2016. © 2015 Society of Plastics Engineers

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“…Alcohols lla-c were easily converted to the chlorides 3a-q using the Vilsmeier reagent (DMF/SOClz) (Hudson & de Spinoza 1976). The treatment of the alcohol Ila with DAST yielded the fluoride 4a along with the symmetrical ether 26, from which it was easily separated (Hudlicky 1988).…”

Section: Functional Modifications a T The Benzylic Positionmentioning

confidence: 99%

Synthesis and Inhibition of Human Leucocyte Elastase by Functionalized N-Aryl Azetidin-2-ones: Effect of Different Substituents on the Aromatic Ring

Joyeau

Felk

Guilaume

et al. 1996

Journal of Pharmacy and Pharmacology

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N-aryl-3,3-difluoroazetidin-2-ones featured by a latent electrophilic methylene quinoniminium function have been synthesized and evaluated as inhibitors of human leucocyte elastase. To promote hydrophobic interactions with the enzyme, to increase the rates of beta-lactam ring opening and of benzylic group departure, or to induce hydrosolubility, these compounds incorporate on their aromatic ring either an alkyl moiety, a methoxy substituent or a carboxylic group. Some of these beta-lactams proved to be good inactivators of human leucocyte elastase.

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Factors in the formation of isomerically and optically pure alkyl halides. Part X. Reactions of saturated aliphatic alcohols with thionyl chloride

Cited by 29 publications

References 0 publications

Synthesis of 1,2-Diamino-1-phenylpropane Diastereoisomers from u-N-Trifluoroacetyl-2-amino-1-phenylpropan-1-ol

Synthesis of 1,2-Diamino-1-phenylpropane Diastereoisomers from u-N-Trifluoroacetyl-2-amino-1-phenylpropan-1-ol

Chlorination of poly(vinyl chloride) model compounds in radical‐complexing solvents

Synthesis and Inhibition of Human Leucocyte Elastase by Functionalized N-Aryl Azetidin-2-ones: Effect of Different Substituents on the Aromatic Ring

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