4436-23-1

Upstream product

• 96-09-3 styrene oxide 
• 21077-81-6 N,N-(dimethylamino)-methylphenylsulfoxonium tetrafluoroborate 
• 4850-49-1 1-phenyl-1,3-propanediol 
• 18776-12-0 3-chloro-1-phenyl-propan-1-ol 
• 100306-31-8 3-bromo-1-phenyl-1-propanol 
• 100-52-7 benzaldehyde 
• 1774-47-6 trimethylsulfoxonium iodide 
• 936-59-4 3-chloropropiophenone 
• 29636-75-7 3-bromo-1-phenylpropan-1-one 
• 758-44-1 N-bromobis(trimethylsilyl)amine 
• 1239865-03-2 triethyl(3-phenylpropoxy)stannane 
• 71-43-2 benzene 
• 26272-85-5 3-iodooxetane 
• 780-69-8 triethoxyphenylsilane 

Downstream Products

• 28547-49-1 (+/-)-1-acetoxy-3-chloro-3-phenylpropane 
• 614-54-0 1-phenylheptan-1-ol 
• 614-54-0 (R)-1-phenylheptanol 
• 614-54-0 (S)-(-)-1-phenyl-1-heptanol 
• 98748-93-7 3-trimethylsiloxy-1-phenylpropyl isocyanide 
• 3524-55-8 4-phenyl-1,3-dioxan-2-one 
• 97838-50-1 1-(3-hydroxy-1-phenylpropyl)cyclohexanol 
• 111787-74-7 3,4-diphenyl-1,3-oxazin-2-one 
• 111787-75-8 3,6-diphenyl-1,3-oxazin-2-one 
• 14097-24-6 1,3-diphenylpropan-1-ol 
• 81548-28-9 2,4-Diphenyl-5,6-dihydro-4H-[1,3]oxazine 
• 117040-48-9 3,3,4-triphenyloxan-2-one 
• 117040-49-0 3,3,6-triphenyloxan-2-one 
• 81548-21-2 2-vinyl-4-phenyl-4H-5,6-dihydro-1,3-oxazine 

Relevant academic research and scientific papers

Rhodium-Catalyzed Regioselective Formal Hydroacylation of Vinyl Epoxides toward Esters Involving β-Carbon Cleavage

Herein we disclose the first example of the formal hydroacylation reactions of vinyl epoxides with chelating aldehydes enabled by rhodium catalysis for the efficient construction of functionalized esters. Detailed investigations of the mechanistic pathway reveal that the presence of a 2-vinyl group is essential in contributing to the success of this regioselective reaction, which might proceed through β-carbon cleavage as the key procedure.

Intermolecular Electrophilic Bromoesterification and Bromoetherification of Unactivated Cyclopropanes

1,3-difunctionalization of cyclopropane is an useful organic transformation. The corresponding 1,3-difunctionalized products are synthetic synthons and building blocks in many organic syntheses. Many existing ring-opening difunctionalization methodologies rely primarily on the use of donor?acceptor cyclopropanes, while the difunctionalization of unactivated cyclopropanes is less exploited. In this research, 1,3-bromoesterification and 1,3-bromoetherification of unactivated cyclopropanes were successfully achieved using N-bromosuccinimide as the brominating agent with high yields and regioselectivity. (Figure presented.).

Palladium-catalyzed hiyama cross-couplings of arylsilanes with 3-Iodoazetidine: Synthesis of 3-arylazetidines

The first palladium-catalyzed Hiyama cross-coupling reactions of arylsilanes with 3-iodoazetidine were described. The protocol provides a convenient access to a variety of useful 3-arylazetidines which are of great interest in pharmaceutical laboratories in moderate to good yields (30%-88%). In addition, this strategy has the advantage of easy operation and mild reaction conditions.

A combined computational and experimental investigation of the oxidative ring-opening of cyclic ethers by oxoammonium cations

The propensity of oxoammonium cations to facilitate the oxidative ring-opening of cyclic ethers to their corresponding distal hydroxy ketones is investigated. The reaction has been evaluated using experimental and computational methods to gain deeper insight into trends in reactivity.

2-Lithiated-2-phenyloxetane: A new attractive synthon for the preparation of oxetane derivatives

A valuable and direct method to access 2-substituted-2-phenyloxetanes by electrophilic quenching of the corresponding 2-lithiated derivative has, for the first time, been described. 2-Lithiated-2-phenyloxetane was found to be configurationally unstable. E

Homolytic reactions of N-bromohexamethyldisilazane with trialkyl(phenylalkoxy) derivatives of silicon and tin

The main product of the photoinduced reaction of N- bromohexamethyldisilazane with trialkyl-(benzyloxy)derivatives of silicon and tin R3MO(CH2)nPh (R = Me, Et; M = Si, Sn; n = 1) is N,N-dibenzylidene-C-phenylmethanediamine (hydrobenzamide). For M = Si, with increase of the length of the methylene chain between the oxygen atom and the phenyl group (n = 2, 3), the similar reaction affords the product of bromination of the benzylic carbon atom R3MO(CH2) n-1CHBrPh. For M = Sn, the reaction results in the formation of 2-phenyloxacycloalkanes PhCHO(CH2)n-1. Pleiades Publishing, Ltd., 2010.

Highly regioselective cleavages and iodinations of cyclic ethers utilizing SmI2

Various functionalized cyclic ethers such as oxiranes, oxetanes, and tetrahydrofurans have been prepared, and the regiochemistry of their ring opening with samarium diiodide and acyl chloride or anhydride has been investigated. Alkyl-substituted oxetane 5 and tetrahydrofurans 1 and 2 show almost no regioselectivity. However, high regioselectivities from the branched cyclic ethers (3, 8, 9, and 10) containing ethereal or hydroxyl moieties have been observed. This is probably the result of the bidentate chelated species between samarium and oxygen.

Novel Synthesis of Cyclopropylaminosulfoxonium Salts from (Dimethylamino)phenylsulfoxonium Methylide

The reactions of (dimethylamino)phenylsulfoxonium methylide with aldehydes gave unusual cyclopropylaminosulfoxonium salts in good yields when 1,8-diazabicycloundec-7-ene (DBU) was used as a base.This ylide reacted with aldehydes to give the corresponding betaines, which resulted in the formation of vinylsulfoxonium salts.The additional ylide reacted with these salts to afford cyclopropylsulfoxonium salts.

The Synthesis of Oxiranes and Oxetanes from 1,2- or 1,3-Halohydrins Using Organoantimony(V) Alkoxide

Tetraphenylstibonium methoxide (1) is an effictive reagent for the synthesis of oxiranes and oxetanes from the corresponding 1,2- and 1,3-halohydrins, respectively.As the reaction conditions are neutral, oxiranes bearing an ester moiety were obtained intact without undergoing solvolysis.In addition, oxetanes, whose preparation was not generally facile, were formed in good yields under mild conditions (60-80 deg C).

IMPROVED SYNTHESIS OF SUBSTITUTED OXETANES, TETRAHYDROFURANS, AND TETRAHYDROPYRANS FROM ω-CHLORINATED CARBOXYLIC ACID CHLORIDES

The reaction of β-chloropropanoyl chloride (1) with a Grignard reagent leads to the corresponding 1,3-chlorohydrin (2), which by treatment with potassium hydride yields a substituted oxetane (4).The use of γ-chlorobutyryl chloride (7) in the same reaction following by refluxing in tetrahydrofuran permits the direct isolation of the corresponding tetrahydrofuran (8) in an one-pot process.Finally, by adding an organomagnesium reagent to δ-chloropentanoyl chloride (11) the corresponding 1,5-chlorohydrin (12) is isolated; the treatment of the latter systems with sodium hydride at tetrahydrofuran reflux leads to the expected substituted substituted tetrahydropyran (13).