Reactions of Grignard reagents with aldehydes and ketones

Reaction of the enolate of methyl vinyl ketone with diphenyl phosphorochloridate yields the phosphate diene, which then undergoes [4 + 2] cycloaddition (eq 7) to form the Diels-Alder adduct in 90% yield. With relatively poor dienophiles like cyclohexenone, Lewis acid catalysts such as may be required.

Percent yield of DiphenylmethanolTable 3.

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In this special synthesis, reducing the benzophenone with zinc dust was used.


IUPAC : Diphenylmethanol ((C6H5)2CHOH)
In pharmaceutical manufacture it is used as a fundamental component
in antihistamines, antihypertensive agents and antiallergenic agents.
It is also used as a fixative in perfumery and as a terminating group in polymerizations
is an irritant to the eyes, skin and respiratory system.

Oxidation-reduction reactions (or redox) reactions, are a type of chemical reaction that involves
a transfer of electrons between two species.

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AB - The Friedel-Crafts polymerization of 2,5-thiophenedicarbonyl dichloride and diphenyl ether in 1,2-dichloroethane afforded only low molecular weight of poly(ether ketone) containing thiophene-ring. In contrast to this, the polymerization in 1-butyl-3-methylimidazolium chloride-aluminum chloride mixture gave high molecular weight polymers. The polymerization in ionic liquid was a new approach to expand possibility of polymer synthesis such as preparation of polymer containing heterocyclic rings. The obtained poly(ether ketone) exhibited good thermal stability and chemical resistance comparable to common poly(ether ketone)s.

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Under the condition of light entrainment, diphenyl phosphate and adjacent groups form free radical ion pair, cause rearrangement (5) and n-cyclohexylmaleimide (6).

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This page looks at the reaction of aldehydes and ketones with Grignard reagents to produce potentially quite complicated alcohols. It is mainly a duplication of the information on these same reactions from a page on Grignard reagents in the section on properties of halogenoalkanes.

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Recrystallize your product using hexanes. Note: If you know the melting point of diphenylmethanol(as you should), then you also recognize one potential problem with recrystallizingfrom hexanes. Talk to your TA about how to solve this potential problem.


These are reactions of the carbon-oxygen double bond, and so aldehydes and ketones react in exactly the same way - all that changes are the groups that happen to be attached to the carbon-oxygen double bond.

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As first demonstrated by Brigl and Müller in the synthesis of glucose and fructose phosphates, diphenyl phosphorochloridate is an excellent reagent for the synthesis of monoalkyl phosphates.

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The reagent has been used in peptide synthesis, one-pot syntheses of sulfinates, sulfinamides, and thiosulfinates, and as an intermediate in the synthesis of , and diphenyl phosphoroisothiocyanatidate. The reagent has been utilized in the study of the -(phosphonooxy)alkyl radical rearrangements, involving the 1,2-migration of phosphate esters.