87372-61-0

Upstream product

• 7393-43-3 tetraallyl tin 
• 939-52-6 4-chloro-1-phenylbutan-1-one 
• 15336-98-8 diallyldibutyltin 
• 106-95-6 allyl bromide 
• 16133-83-8 tetrahydro-2-phenylfuran 
• 33553-82-1 4-chloro-1-phenyl-1-butanol 
• 2622-05-1 allylmagnesium bromide 

Relevant academic research and scientific papers

Water opens the door to organolithiums and Grignard reagents: Exploring and comparing the reactivity of highly polar organometallic compounds in unconventional reaction media towards the synthesis of tetrahydrofurans

It has always been a firm conviction of the scientific community that the employment of both anhydrous conditions and water-free reaction media is required for the successful handling of organometallic compounds with highly polarised metal-carbon bonds. Herein, we describe how, under heterogeneous conditions, Grignard and organolithium reagents can smoothly undergo nucleophilic additions to γ-chloroketones, on the way to 2,2-disubstituted tetrahydrofurans, "on water", competitively with protonolysis, under batch conditions, at room temperature and under air. The reactivity of the above organometallic reagents has also been investigated in conventional anhydrous organic solvents and in bio-based eutectic and low melting mixtures for comparison. The scope and limitations of this kind of reaction are discussed.

Gated access to α-lithiated phenyltetrahydrofuran: Functionalisation via direct lithiation of the parent oxygen heterocycle

Cycloreversion of α-lithiated phenyltetrahydrofuran was successfully tamed at -78 °C in a non-coordinating solvent in the presence of TMEDA. This anion showed excellent nucleophilicity and could be intercepted with a variety of structurally different electrophiles to give 2,2-disubstituted derivatives which can be further elaborated to γ-butyrolactones. The Royal Society of Chemistry 2013.

Multi-product classes obtained from allylation of α-halo ketones with allylzinc bromide

An efficient, one-pot synthesis procedure for the preparation of allylic epoxides, aldehydes and homoallylic alcohols (see scheme) has been described. The three industrial products were synthesized by the reaction of allylzinc bromide with a-halo ketones

The formation of cyclic ethers from diallyldibutyltin and halo ketones catalyzed by tetraethylammonium chloride

The cyclization reaction of diallyldibutyltin and α- or γ-halo ketones, especially chloro-substituted ketones, effectively proceeds in the presence of a catalytic amount of tetraethylammonium chloride, producing the corresponding 2-allyloxiranes or 2-ally

Synthesis of Substituted Cyclic Ethers from Halo Ketones and Halo Aldehydes by Palladium-Catalyzed Coupling with Organotin Reagents

The palladium-catalyzed reaction of a variety of halo ketones or halo aldehydes with acetonyl- and allyltin reagents gives cyclic ethers in good yields.Oxiranes, oxetanes, and tetrahydrofurans can be obtained under mild reaction conditions.The use of palladium catalyst containing chiral monophosphine ligands gave a small enantiomeric excess (up to 19percent) of a chiral oxirane from an α-halo ketone.The allyl- and acetonyloxirane products tend to undergo further transformations in prolonged reactions: allyloxiranes rearrange to α-allyl aldehydes and acetonyloxiranes dehydrate to give substituted furans.The mechanism of the reaction appears to involve addition of the organotin ligand to the carbonyl, followed by palladium(II)-catalyzed cyclization of the tin alkoxides.