58052-51-0

Usage

InChI:InChI=1/C14H16N2O2/c1-13(17,11-7-3-5-9-15-11)14(2,18)12-8-4-6-10-16-12/h3-10,17-18H,1-2H3

Upstream product

• 613-90-1 benzoyl cyanide 
• 1122-62-9 2-acetylpyridine 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 59576-32-8 1,2-di(pyridin-2-yl)ethanone 

Relevant academic research and scientific papers

Oxidative Ring-Opening Reaction of Cyclopropanone Acetals with Carbonyl Compounds via Photoinduced Electron Transfer. Generation of a β-Carbonyl Radical Species and Its Application to the Synthesis of γ-Hydroxy Ester Derivatives

Photoinduced electron transfer (PET) reactions of 2-substituted or 2,2-disubstituted cyclopropanone methyl trialkylsilyl acetals 1a-e,g and 1-siloxy-2-oxabicyclohexane (1f) with carbonyl compounds 2 (benzophenone (2a), acetophenone (2b), 2-acetonaphthone (2c), 2-acetylpyridine (2d), 4-acetylbenzonitrile (2e), 2,3-butanedione (2f), and benzoyl cyanide (2g)) were examined in the presence of Mg(ClO4)2.Carbon-carbon bond coupling products (γ-hydroxy esters 3 or their derivative butyrolactones 4) between 1 and 2 were formed in good yields.A mechanism is proposed for the product formation which is initiated by the single electron transfer (SET) from 1 to the excited state of 2.The set generates a transient pair of ion radicals, i.e. a ring-opened sec- or tert-β-carbonyl radical from 1 and a ketyl radical ion from 2 stabilized by the Mg salt.This realizes a novel type of carbon-carbon bond formation at the sterically crowded β-position of propanoates.

A Novel Reaction Type Promoted by Aqueous Titanium Trichloride. Synthesis of Allylic Pinacols

Electron-withdrawing substituted carbonyl compounds which are allowed to react with 2 equiv of aqueous titanium trichloride selectively add to the carbonyl carbon atom of α,β-unsaturated aldehydes.Highly functionalized allylic pinacols are obtained in good yields under very simple experimental conditions.The fundamental role played by the titanium(III) ion is discussed.

A Novel Reaction Type Promoted by Aqueous Titanium Trichloride. Synthesis of Unsymmetrical 1,2-Diols

Electron-withdrawing substituted carbonyl compounds when allowed to react with 2 equiv of aqueous titanium trichloride in the presence of acetone, acetaldehyde, or benzaldehyde afford unsymmetrical 1,2-diols in high yields under very simple experimental conditions.