Carbon-Carbon Bond Formation by Use of Chloroiodomethane as a C1 Unit. I. Formation of Chloromethyltriphenylphosphonium Iodide, and Its Application for the Wittig Chloromethylenation of Aldehydes and Ketones

doi:10.1246/BCSJ.52.1197

Paper

Carbon-Carbon Bond Formation by Use of Chloroiodomethane as a C1 Unit. I. Formation of Chloromethyltriphenylphosphonium Iodide, and Its Application for the Wittig Chloromethylenation of Aldehydes and Ketones

Published Apr 1, 1979 · S. Miyano, Y. Izumi, Katsuo Fujii

Bulletin of the Chemical Society of Japan

Q2 SJR score

22

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0

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Abstract

Chloromethyltriphenylphosphonium iodide has been prepared by the reaction of chloroiodomethane with triphenylphosphine. Upon treatment with potassium t-butoxide in t-butyl alcohol, the phosphonium iodide was converted into chloromethylenetriphenylphosphorane; this in turn was used for the Wittig reaction of aldehydes and ketones into the corresponding chloroolefins of the type RCH=CHCl and RR′C=CHCl in good to moderate yields. The configurations of these chloroolefins were assigned on the basis of NMR spectral studies. Direct conversion of benzaldehyde into phenylacetylene was also achieved using the phosphonium salt and excess potassium t-butoxide.

Study Snapshot

Chloromethyltriphenylphosphonium iodide can be used for the Wittig reaction of aldehydes and ketones to produce chloroolefins with good to moderate yields, and also for direct conversion of benzaldehyde into phenylacety

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Carbon-Carbon Bond Formation by Use of Chloroiodomethane as a C1 Unit. I. Formation of Chloromethyltriphenylphosphonium Iodide, and Its Application for the Wittig Chloromethylenation of Aldehydes and Ketones

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References

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Oxygen greatly accelerates the cyclopropanation of olefins, yielding cyclopropanes with 70-100 % yields, using a free-radical-chain mechanism.

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Excess zinc can lead to styrene formation from benzaldehyde, with chloroiodomethane providing the best result, while polychloromethanes do not yield styrene.

Basen‐induzierte Eliminierungen, III. Der Einfluß von Stereochemie und Substituenten auf die Reaktivität von Vinylchloriden

Stereochemistry and substituents influence the reactivity of vinyl chlorides, with electron-rich R having a lower reaction rate than electron-poor R.

Studies in phosphinemethylene chemistry : XIII. Routes to triphenylphosphine-halomethylenes and -dihalomethylenes☆

Phenyllithium on (bromomethyl)triphenylphosphonium bromide leads to a nearly equimolar mixture of triphenylphosphinebromomethylene and triphenylphosphinemethylene, with (iodomethyl)tripheny

Über die Herstellung von Vinyläthern, Vinylthioäthern und Vinylhalogeniden auf der Phosphylen-Basis; IV. Mitteil. über Phosphin-alkylene als olefinbildende Reagenzien

Phosphin-alkylene can be used as an olefin-forming reagent for the production of vinyl ethers, vinylthioethers, and vinylhalogenides.

Citations

Site- and Stereoselective Synthesis of Alkenyl Chlorides by Dual Functionalization of Internal Alkynes via Photoredox/Nickel Catalysis.

This study presents a redox-neutral, atom-economical method for synthesizing valuable alkenyl chlorides from internal alkynes and organochlorides, enabling site- and stereoselective addition of organochlorides to alkynes.

Metal-free POCl3 promoted stereoselective hydrochlorination of ethynylated azaheterocycles.

POCl3 efficiently hydrochlorinates ethynylated azaheterocycles under metal-free conditions, resulting in versatile intermediates for organic synthesis and metal-free heterocycle synthesis.

Studies toward the Synthesis of Smenamide A, an Antiproliferative Metabolite from Smenospongia aurea: Total Synthesis of ent-Smenamide A and 16-epi-Smenamide A

This study successfully synthesized ent-smenamide A and 16-epi-smenamide A, two antiproliferative molecules from Smenospongia aurea, with a 2.6 and 2.5% overall yield, establishing previously unknown relative and absolute configurations.

Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl.

This study presents a regioselective anti-hydrochlorination of unactivated alkynes with palladium(II) acetate, providing access to a broad array of substituted alkenyl chlorides with high regioselectivity and excellent yields.

A new entry of highly nucleophilic CHBr3–TiCl4–Mg system for the stereoselective synthesis of 1-alkenyl bromides

The CHBr3-TiCl4-Mg system allows for the simple, practical, and stereoselective synthesis of 1-alkenyl bromides, primarily resulting in (E)-vinyl bromides.