90448-23-0

Upstream product

• 59036-42-9 4-methyl-1-(3-chloro-2-propenoxy)benzene 
• 542-75-6 E/Z-1,3-Dichloropropene 
• 106-48-9 4-chloro-phenol 
• 13997-70-1 1-allyloxy-4-chlorobenzene 
• 109392-03-2 C₁₅H₁₄Cl₄OSe 

Downstream Products

• 16336-27-9 6-chloro-2H-chromene 
• 102117-77-1 4-chloro-2-(3-chloro-2-propenyl)phenol 
• 102117-78-2 4-chloro-2-(3-chloro-2-propenyl)-1-(3-chloro-2-propenoxy)benzene 
• 106-48-9 4-chloro-phenol 

Relevant academic research and scientific papers

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.

CATALYTIC REARRANGEMENT OF THE γ-CHLOROALLYL ETHERS OF PHENOLS

The catalytic rearrangement of the γ-chloroallyl ethers of phenol, p- and o-cresol, p- and o-chlorophenol, and 2,4-dichlorophenol takes place by an intermolecular mechanism with the formation of alkenylphenols without inversion of the allylic unit.The transformation of the ethers with a CH3 group (ortho or para) in the benzene ring takes place under milder conditions than that of ethers with a chlorine atom at the same positions.

THERMAL REARRANGEMENT OF THE γ-CHLOROALLYL ETHERS OF PHENOLS. THE FORMATION OF 2H-CHROMENES

The termal rearrangement of the γ-chloroallyl ethers of phenols takes place as an intramolecular -sigmatropic Claisen rearrangement.The final compounds are not the Claisen phenols but the products from their subsequent transformations, i.e., 2H-chrom