69485-62-7

Upstream product

• 41596-88-7 1-lithio-1-(phenylthio)-cyclopropane 
• 18328-11-5 3-benzyl propionaldehyde 
• 104-53-0 3-phenyl-propionaldehyde 
• 3607-17-8 3-bromopropyltriphenylphosphonium bromide 

Downstream Products

• 74312-54-2 (E)-4-methyl-1-phenyl-2,4-pentadiene 
• 344359-71-3 methyl 7-phenylhept-4-enoate 
• 27356-93-0 1-(3-phenylpropyl)cyclopropane-1-carboxylic acid 
• 344359-68-8 (E)-7-phenylhept-4-enoic acid 
• 1417163-69-9 (Z)-ethyl 6-bromo-2-methylene-9-phenyl-6-nonenoate 
• 1417163-70-2 (E)-ethyl 6-bromo-2-methylene-9-phenyl-6-nonenoate 
• 117754-20-8 1-Methyl-4-((E)-6-phenyl-1-phenylselanyl-hex-3-ene-3-sulfonyl)-benzene 

Relevant academic research and scientific papers

Oxidative Ring Expansion of Cyclobutanols: Access to Functionalized 1,2-Dioxanes

Cyclobutanols undergo an oxidative ring expansion with Co(acac)2 and triplet oxygen to give 1,2-dioxanols. The formation of an alkoxy radical drives the regioselective cleavage of the ring on the more substituted side before insertion of molecular oxygen. The reaction is particularly effective on secondary cyclobutanols but works also on certain tertiary alcohols. Further substitution with neutral nucleophiles under catalytic Lewis acid conditions led to original 1,2-dioxanes with a preferred 3,6-cis-configuration.

Iron-Catalyzed Regioselective Alkenylboration of Olefins

The first examples of an iron-catalyzed three-component synthesis of homoallylic boronates from regioselective union of bis(pinacolato)diboron, an alkenyl halide (bromide, chloride or fluoride), and an olefin are disclosed. Products that bear tertiary or quaternary carbon centers could be generated in up to 87 % yield as single regioisomers with complete retention of the olefin stereochemistry. With cyclopropylidene-containing substrates, ring cleavage leading to trisubstituted E-alkenylboronates were selectively obtained. Mechanistic studies revealed reaction attributes that are distinct from previously reported alkene carboboration pathways.

Synthesis of Fluorinated Homoallylic Compounds by Fluoroalkyl Radical Mediated Ring Opening of Methylenecyclopropanes

The fluoroalkyl (Rf) radical mediated ring opening of methylenecyclopropanes (MCPs) 1 and subsequent atom transfer were investigated. In the first part, a copper-initiated radical reaction of Rf-X (X = I, Br) with MCP 1 gave homoallylic halides 2 in excellent yields. Similarly, radical reaction of the RfTMS/CsF/PhI(OCOR)2 system with MCP 1 led to homoallylic alcohol esters 3 in moderate to good yields. An efficient synthesis of fluoroalkyl (Rf)-substituted homoallylic halides 2 and homoallylic alcohol esters 3 by fluoroalkyl radical mediated ring opening of methylenecyclopropanes (MCPs) 1 followed by an atom-transfer process is developed.

Bromine radical-mediated sequential radical rearrangement and addition reaction of alkylidenecyclopropanes

Bromine radical-mediated cyclopropylcarbinyl-homoallyl rearrangement of alkylidenecyclopropanes was effectively accomplished by C-C bond formation with allylic bromides, which led to the syntheses of 2-bromo-1,6-dienes. A three-component coupling reaction

PtCl2-catalyzed rearrangement of methylenecyclopropanes

Alkylidenecyclopropanes readily convert into cyclobutene derivatives on treatment with catalytic amounts of PtCl2. The reaction is strongly accelerated when performed under an atmosphere of CO (1 atm). The resulting cyclobutenes are isolated in