15131-55-2

Usage

Safety Profile

Moderately toxic by skin contact.Mildly toxic by ingestion. When heatedto decomposition it emits acrid smoke and irritatingfumes.

InChI:InChI=1/C10H14O/c1-2-6-9(5-1)11-10-7-3-4-8-10/h1,3,5,7,9-10H,2,4,6,8H2

Upstream product

• 3212-60-0 cyclopent-2-enol 
• 96-40-2 2-cyclopenten-1-yl chloride 
• 124-63-0 methanesulfonyl chloride 
• 930-30-3 cyclopent-2-enone 
• 109391-80-2 C₁₁H₁₃Cl₃Se 
• 542-92-7 cyclopenta-1,3-diene 

Downstream Products

• 78877-81-3 4-(cyclopenten-2-yl)-2,6-dimethylphenol 
• 78877-80-2 4-(cyclopenten-2-yl)-o-cresol 
• 6627-84-5 p-(cyclopent-2-en-1-yl)phenol 
• 120-92-3 cyclopentanone 
• 78877-83-5 4-(cyclopenten-1-yl)-2,6-dimethylphenol 
• 78877-82-4 4-(cyclopenten-1-yl)-o-cresol 
• 877-46-3 4-(1-cyclopenten-1-yl)phenol 
• 694-35-9 3-ethylcyclopentene 

Relevant academic research and scientific papers

Multiple Olefin Metathesis Polymerization That Combines All Three Olefin Metathesis Transformations: Ring-Opening, Ring-Closing, and Cross Metathesis

We demonstrated tandem ring-opening/ring-closing metathesis (RO/RCM) polymerization of monomers containing two cyclopentene moieties and postmodification via insertion polymerization. In this system, well-defined polymers were efficiently formed by tandem cascade RO/RCM reaction pathway. Furthermore, these polymers could be transformed to new A,B-alternating copolymers via a sequential cross metathesis reaction with a diacrylate. Additionally, we demonstrated the concept of multiple olefin metathesis polymerization in which the dicyclopentene and diacrylate monomers underwent all three olefin metathesis transformations (ring-opening, ring-closing, and cross metathesis) in one shot to produce A,B-alternating copolymer.

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.

ETHER FORMATION FROM ALLYLIC ALCOHOLS CATALYZED BY SAMARIUM TRICHLORIDE

The behaviour of various allylic alcohols in the presence of catalytic amounts of SmCl3 (by heating in 1,2-dichloroethane) has been studied.Diallyl ethers are obtained in many cases in good yields.Mixed allyl alkyl ethers are also prepared if 2-5 equivalents of an aliphatic alcohol is present.The reactions are interpreted as proceeding through a pseudo allylic carbonium intermediate initiated by a preliminary complexation of the allyl hydroxyl to the samarium ion.