71104-85-3

Upstream product

• 114095-76-0 1-bromo-4-(1-methoxy-but-3-enyl)benzene 
• 90921-71-4 4-(dimethoxymethyl)benzonitrile 
• 762-72-1 allyl-trimethyl-silane 
• 53582-00-6 ethyl trans-2-(p-bromophenyl)-1-cyclopropanecarboxylate 
• 114095-66-8 trans-2-(p-cyanophenyl)cyclopropanemethanol 
• 114095-64-6 (1S*, 2S*)-(2-(4-bromophenyl)cyclopropyl)methanol 
• 1122-91-4 4-bromo-benzaldehyde 
• 106650-98-0 1-(4-bromophenyl)but-3-en-1-ol 
• 67-56-1 methanol 
• 71104-65-9 trans-<2-(p-cyanophenyl)cyclopropyl>methyl acetate 

Relevant academic research and scientific papers

ARYLCYCLOPROPANE PHOTOCHEMISTRY. UNUSUAL AROMATIC SUBSTITUENT EFFECTS ON THE PHOTOCHEMICAL REARRANGEMENT OF (2-ARYLCYCLOPROPYL)METHYL ACETATES TO 1-ARYLHOMOALLYL ACETATES.

Irradiation of trans(2-arylcyclopropyl)methyl acetates a 4-butenyl-1-arylacetate (7a,b,d-h) via an ionic mechanism from the singlet state. Similar rearrangements occurred with exo-(1,1a,6,6a-tetrahydrocycloprop left bracket a right bracket inden-1-yl)methyl acetate and the 4-cyano derivative. Excited state reaction rate constants were determined from reactant fluorescence lifetimes and product quantum yields. It is concluded that the rate-determining step involves conversion of the initially formed aromatic excited state to a reactive cyclopropane excited state and that cyclopropane to aromatic ring charge transfer enhances this process.

Electrogenerated Acid-Catalyzed Reactions of Acetals, Aldehydes, and Ketones with Organosilicon Compounds, Leading to Aldol Reactions, Allylations, Cyanations, and Hydride Additions

Exquisite use of electrogenerated acid (EG acid) in the silicon-mediated acid-catalyzed reactions; e.g., aldol reactions, allylations, cyanations, and hydride additions is described.The aldol reaction of acetals 1 with enol trimethylsilyl ethers 3 and 1,2-bis(trimethylsiloxy)alkenes 4 gives the corresponding adducts 5 and 6, respectively.The reaction proceeds smoothly with EG acid derived from perchlorate salts such as LiClO4, n-Bu4NClO4, and Mg(ClO4)2 in dichloromethane using platinum electrodes.The amount of electricity required to complete the reaction implies a cationic process which is mediated by the trimethylsilyl moiety.This aldol reaction is further developed with unprotected carbonyl compounds 2 with 3, giving the trimethylsilyl ethers of the adducts 7.Further utility of this EG acid as a catalyst for a chain reaction is exemplified by the successful application in the following conversions: (1) The allylation of acetals 1 with allyltrimethylsilane (8) to give 9, (2) the cyanation of acetals 1 and unmasked 2 with trimethylsilyl cyanide (10) to give 11, 12, and 13, and (3) the hydride addition of acetals 1 with triethylsilane (14) to give 15.