692-72-8

Usage

InChI:InChI=1/C5H7ClO2/c1-4(6)3-8-5(2)7/h1,3H2,2H3

Upstream product

• 78-88-6 2,3-Dichloroprop-1-ene 
• 127-08-2 potassium acetate 
• 109391-92-6 (3-acetoxy-2-chloropropyl)phenylselenium dichloride 
• 5976-47-6 2-chloroallyl alcohol 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 

Downstream Products

• 73336-27-3 2-methyl-2-(2-chloropropenyl)-1,3-cyclohexanedione 
• 92825-40-6 2-prenyl-2-(2-chloropropenyl)-1,3-cyclohexanedione 
• 92825-39-3 2-allyl-2-(2-chloropropenyl)-1,3-cyclohexanedione 
• 122570-94-9 [1-(Benzhydrylidene-amino)-3-chloro-but-3-enyl]-phosphonic acid diethyl ester 
• 32933-07-6 1-(2,4-dimethyl-furan-3-yl)-ethanone 
• 6148-33-0 ethyl 2,4-dimethylfuran-3-carboxylate 
• 187029-65-8 dimethyl (2-chloroprop-2-en-1-yl)(methyl)malonate 
• 403855-58-3 methyl 2-(methylcarboxy)-2-methyl-4-phenoxypent-4-enoate 

Relevant academic research and scientific papers

Sequential Palladium-Catalyzed Allylic Alkylation/retro-Dieckmann Fragmentation Strategy for the Synthesis of α-Substituted Acrylonitriles

A straightforward synthesis of α-substituted acrylonitriles is described using 4-cyano-3-oxotetrahydro-thiophene (c-THT) as an acrylonitrile surrogate. This unprecedented two-step sequence featuring a palladium-catalyzed allylic alkylation (Pd-AA) and a retro-Dieckmann fragmentation provides a general entry into diversely substituted 1,4-dienes.

Palladium-Catalyzed Asymmetric Allylic Alkylation of 4-Substituted Isoxazolidin-5-ones: Straightforward Access to β2,2-Amino Acids

We report here an unprecedented and highly enantioselective palladium-catalyzed allylic alkylation applied to 4-substituted isoxazolidin-5-ones. Ultimately, the process provides a straightforward access to β2,2-amino acids bearing an all-carbon quaternary stereogenic center in great yields and a high degree of enantioselectivity.

Highly Enantioselective, Base-Free Synthesis of α-Quaternary Succinimides through Catalytic Asymmetric Allylic Alkylation

The synthesis of diversely substituted five-membered ring succinimide derivatives is reported featuring a direct, base-free, palladium-catalyzed asymmetric allylic alkylation. The method allows a straightforward access to the desired heterocyclic scaffold bearing an all-carbon α-quaternary stereogenic center in high yields and good to excellent enantioselectivities. To further demonstrate the synthetic utility of the method, the allylated products were further converted to various versatile chiral building blocks, including a chiral pyrrolidine and a spirocyclic derivative, using selective transformations.

A New Platinum Complex Catalyzed Reaction Involving Nucleophilic Substitution at the Central Carbon Atom of the π-Allyl Ligand

The reaction of 2-chloro-allyl acetate with sodium ethyl acetoacetate in the presence of a platinum-(0) complex gave furan derivatives. The key feature of this new platinum-catalyzed reaction is the nucleophilic substitution at the central carbon atom of π-allyl complexes. The regioselectivity of the nucleophilic attacks (central or terminal) is dependent on the pKa of the nucleophile. In addition, a labeling experiment revealed that a rapid syn-anti isomerization of the (π-allyl) platinum complexes occurs.

HYDROLYTIC SELENOXIDE ELIMINATION REACTION FOR THE PREPARATION OF 2-CHLORO-1-OLEFINS

2-Chloro-1-olefins were synthesized in a regiocontrolled way from terminal olefins by a sequence involving Markownikoff-addition of PhSeCl, chlorination of the resulting β-chloroalkyl phenyl selenides with SO2Cl2 and, after recrystallization, hydrolysis/s

Phenylselenium Trichloride in Organic Synthesis. Reaction with Unsaturated Compounds. Preparation of Vinylic Chlorides via Selenoxide Elimination

Phenylselenium trichloride, PhSeCl3, was reacted with a number olefinic compounds to produce (β-chloroalkyl)phenylselenium dichlorides.The addition was anti stereospecific and irreversible.The presence of an oxygen substituent (acyloxy or aryloxy group) in the allylic position of the olefin directed the attack of PhSeCl3 to occur regiospecifically anti-Markovnikov to give a (β-acyloxy/aryloxy-β'-chloroalkyl)phenylselenium dichloride.When the (β-chloroalkyl)phenylselenium dichlorides were treated in methylene chloride with aqueous sodium hydrogen carbonate, the selenium dichloride moiety was readily hydrolyzed to a selenoxide, which underwent the usual selenoxide elimination reaction to produce an allylic or a vinylic chloride.Symmetrical olefins containing no allylic hydrogens were converted to vinylic chlorides with retention of olefin geometry.Olefins containing a directing oxygen substituent in the allylic position afforded vinylic chlorides where the vinylic halogen atom was oriented 1,3 to the oxygen substituent (E/Z mixture).Other olefins afforded mixtures of allylic and vinylic halides in varying proportions.The reaction of phenyselenium tribromide, PhSeBr3, with some olefinic compounds was also investigated.This material showed the same stereo- and regiochemical behavior as PhSeCl3 in its addition reactions.However, the adducts were not useful for the preparation of vinylic or allylic bromides by using the hydrolytic selenoxide elimination reaction.