Factors Governing the Reaction of the Benzyl Grignard Reagent. I. Reactions with Acetaldehyde, Chloral, and Trifluoroacetaldehyde

Benkeser, Robert A.; Johnston, Thomas E.

doi:10.1021/ja00962a026

Cited by 19 publications

(6 citation statements)

References 4 publications

(5 reference statements)

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“…Such products have been observed with benzylmagnesium chloride (3,4) and have recently been reported for the benzophenone sodium ketyl (5). The factors controlling the extent of ring substitution are not fully established but a solvent effect has been noted both for the benzyl Grignard and for the benzophenone ketyl.…”

Section: Discussionsupporting

confidence: 54%

Anomalous reaction products from the alkylation of the disodium adduct of benzophenone anil

Smith¹

1968

Can. J. Chem.

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Treatment of the disodium adduct of benzophenone anil with isopropyl bromide produced substantial amounts of a by-product as well as the previously reported product, 2-methyl-N,1,1-triphenylpropylamine. This by-product is shown to be N(o-isopropylbenzhydryl)aniline, formed by alkylation of the adduct on the aromatic ring.The structural proof relies both upon the synthesis of the unknown amine and upon the oxidation of the unknown amine to o-isopropylbenzophenone.

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Section: Discussionsupporting

confidence: 54%

Anomalous reaction products from the alkylation of the disodium adduct of benzophenone anil

Smith¹

1968

Can. J. Chem.

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“…Additionally, anhydrous solvents typically used in Grignard reactions, diethyl ether and tetrahydrofuran (THF), are expensive to purchase or are dried using highly reactive sodium metal (Na 0 ). 11,12 These circumstances limit the accessibility and success of Grignard reactions performed in tropical countries, forcing some universities to omit this experiment from their laboratory classes. Over the years, several journal articles have introduced modifications and improvements in protocols regarding both the formation of Grignard reagents and their subsequent reactions with aldehydes and ketones to form secondary or tertiary alcohols, respectively.…”

Section: ■ Introductionmentioning

confidence: 99%

“…While this may not be a source of concern in temperate countries where dry conditions persist for some periods of the year, the same cannot be said to be true for tropical countries where humidity is high all of the time. Additionally, anhydrous solvents typically used in Grignard reactions, diethyl ether and tetrahydrofuran (THF), are expensive to purchase or are dried using highly reactive sodium metal (Na 0 ). , These circumstances limit the accessibility and success of Grignard reactions performed in tropical countries, forcing some universities to omit this experiment from their laboratory classes.…”

Section: Introductionmentioning

confidence: 99%

“…Over the years, several journal articles have introduced modifications and improvements in protocols regarding both the formation of Grignard reagents and their subsequent reactions with aldehydes and ketones to form secondary or tertiary alcohols, respectively. , Comparative studies regarding Grignard reactions in chemical education have also looked at the addition of a catalyst , or using room-temperature ionic liquids (RTILs) , to decrease the number of “failed reactions”. Still, others have prescribed the use of easier methods such as the use of a premade Grignard reagent or the use of sonication to activate the reaction …”

Section: Introductionmentioning

confidence: 99%

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Facile Grignard Reaction Demonstration Using Molecular Sieved Dried Solvent

Reyes

Tumaneng

2021

ACS Chem. Health Saf.

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Methods involving C–C bond formation are continuously being innovated due to their importance in the creation and modification of important organic molecules. The classic Grignard reaction demonstrates C–C bond formation with reagents that are usually accessible in undergraduate laboratory classes. Oftentimes, to make the Grignard reaction viable, the reactions are assisted by heating at elevated temperatures or with the use of a catalyst accompanied by solvents that have been dried using highly reactive sodium metal (Na0)conditions which increase the risk of a laboratory fire or explosion. For this work, a method to conduct Grignard reactions under mild conditions utilizing sand-paper-polished Mg ribbons and solvent dried using molecular sieves was developed. The conscientious, accessible, and easy-to-follow preparation of both the solvent and the Mg ribbons is found to contribute more to the percent conversion of reagents to products. The average percent conversion with the proposed method ranged from 76.8% to 99.5% based on 1H NMR results. This makes the Grignard demonstration possible even for the most humid, tropical locations.

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“…The solvents were freshly distilled from sodium-potassium alloy (Et 2 O, n-pentane) or potassium (dem, thf, n-hexane) prior to use and degassed. The reactants were commercially available or synthesized according to published procedures (S(N t Bu) 2 , [18] [(thf)Li 2 {H 2 CS(N t Bu) 2 }] 2 (1), [62,66] Me 3 P, [276] MePh 2 P, [276] [Li(H 2 CPMe 2 )], [277] [Li(H 2 CPPh 2 ], [278] BzMgCl [279] ). The phosphanes, arsanes, and arsenane oxides are hazardous compounds and should be handled with caution in a well ventilated hood only.…”

Section: Generalmentioning

confidence: 99%

Syntheses and Electron Density Determination of Novel Polyimido Sulfur Ylides

Deuerlein¹

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Die vorliegende Arbeit wurde in der Zeit von Januar 2004 bis September 2007 im Arbeitskreis von Prof. Dr. D. Stalke an den Instituten für Anorganische Chemie der Universitäten Würzburg und Göttingen angefertigt. An dieser Stelle soll all jenen Dank ausgesprochen werden, die zum Gelingen dieser Arbeit beigetragen haben. Zu allererst möchte ich mich bei Herrn Prof. Dr. D. Stalke bedanken. Sowohl die gewährten wissenschaftlichen Freiheiten, als auch die stete Diskussionsbereitschaft, das angenehme Arbeitsklima und den festen Glauben, dass mein Ylid sich doch noch als Schatz erweist, habe ich sehr geschätzt. Dem gesamten Arbeitskreis, inklusive des zugehörigen Umfeldes, danke ich für die gute Stimmung und die Hilfestellungen bei meinen vielfältigen Problemen, v. a. in der Anfangszeit. Herr Dr. Dirk Leusser hat mich in die Kristallographie und die Elektronendichteuntersuchungen eingeführt, wofür ich ihm sehr dankbar bin. Auch die Motivation und Geduld, immer wieder einen Versuch mit meinem Ylid durchzustehen, war vorbildlich. Gleiches gilt für die viele Arbeit, welche die Hilfe bei der Datenauswertung mit sich brachte. Noch mehr weiß ich aber die Freundschaft zwischen mir Konservativem und einem Linken zu schätzen. Herrn Dipl. Chem. Holger Ott danke ich für die tollen Ergebnisse aus einem großartigen F-Praktikum. Viel mehr genieße ich aber die Freundschaft, die sicher sehr schnell zwischen uns entwickelt hat. Frau Ulrike Flierler danke ich zusammen mit Herrn Dr. Thomas Stey für das gute "team-work" und die sehr angenehm zusammen verbrachte Zeit. Ohne diese Freundschaften hätte ich die Durststrecken dieser Arbeit sich nicht so gut überstanden. Dem Rest der Würzburger-Connection, den Herren Dipl. Chem. Gerald Schwab und Thomas Schulz, danke ich wie Holger, Ulli und Dirk dafür, dass ich nicht ganz allein ins Feindesland musste. Meinem Admin-Vorgänger Herrn Dr. Alex Murso, sowie meinem Nachfolger in spe Herrn Daniel Kratzert, danke ich für die Entlastung bei den täglichen Sorgen mit dem Rechnersystem, sowie für die angenehme gemeinsame Zeit im Labor.

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Factors Governing the Reaction of the Benzyl Grignard Reagent. I. Reactions with Acetaldehyde, Chloral, and Trifluoroacetaldehyde

Cited by 19 publications

References 4 publications

Anomalous reaction products from the alkylation of the disodium adduct of benzophenone anil

Anomalous reaction products from the alkylation of the disodium adduct of benzophenone anil

Facile Grignard Reaction Demonstration Using Molecular Sieved Dried Solvent

Syntheses and Electron Density Determination of Novel Polyimido Sulfur Ylides

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