4392-26-1

Basic information

• Product Name: Benzene,(1-chloro-2-propenyl)-
• CAS NO: 4392-26-1
• Molecular Weight: 152.623
• Mol File: 4392-26-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzene,(1-chloro-2-propenyl)- (CAS DataBase Reference)
• NIST Chemistry Reference: Benzene,(1-chloro-2-propenyl)- (4392-26-1)
• EPA Substance Registry System: Benzene,(1-chloro-2-propenyl)- (4392-26-1)

Safety Data

• Hazardous Substances Data: 4392-26-1(Hazardous Substances Data)

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 2350-09-6 N-chloro-N-methylmethane sulphonamide 
• 96233-07-7 3-phenyl-allyl diphenyl phosphate 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 104-54-1 3-Phenylpropenol 

Downstream Products

• 2687-12-9 cinnamyl chloride 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 479675-41-7 triphenyl-(1-phenyl-allyl)-silane 

Relevant articles and documents

Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes

Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. We report a photocatalytic and diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes. Quantum mechanical calculations (uM06-2X and DLPNO), including TD-DFT calculations, and experimental studies provide evidence for the energy transfer from an iridium photocatalyst to the allylic chloride substrate followed by C-Cl homolytic cleavage. Subsequent Cla￠ radical migration forms a localized triplet 1,3-diradical intermediate that, after intersystem crossing, undergoes ring-closing to form the desired product. The mild reaction conditions are compatible with a broad range of functional groups to generate chlorocyclopropanes in high yields and diastereoselectivities. A more efficient process is developed by addition of a catalytic amount of a nickel complex, and we propose a novel role for this cocatalyst to recycle an allyl chloride byproduct generated in the course of the reaction. The reaction is also shown to be stereoconvergent, as an E/Z mixture of cinnamyl chlorides furnish the anti-chlorocyclopropane product in high diastereoselectivity. We anticipate that the use of a visible light activated photocatalyst to transform substrates in combination with a transition metal catalyst to recycle byproducts back into the catalytic cycle will provide unique opportunities for the discovery of new reactivity.

Regio- and Stereoselective Conversion of Allylic Alcohols to Halides via Allylic Phosphates

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