77743-40-9

Upstream product

• 108-11-2 Methyl isobutyl carbinol 
• 98-88-4 benzoyl chloride 
• 85106-61-2 1-benzoyl-3-benzylimidazolium chloride 
• 2568-06-1 (2S,6S)-4,4,6-Trimethyl-2-phenyl-[1,3]dioxane 
• 330188-15-3 2-Phenyl-4,4,6-trimethyl-1,3-dioxan 

Relevant academic research and scientific papers

Radical Transformation of Aliphatic C-H Bonds to Oxime Ethers via Hydrogen Atom Transfer

Herein, we describe a strategy for conversion of aliphatic C-H bonds to oxime ethers via hydrogen atom transfer. In this strategy, the decatungstate anion and sulfate radical play complementary roles in the abstraction of hydrogen atoms from primary, secondary, and tertiary C-H bonds of alkanes. The easy accessibility of alkanes and the broad substrate scope, mild conditions, and excellent regioselectivity of these reactions make this strategy applicable for the transformation of raw materials to high-value chemicals.

Silver-mediated oxidative aliphatic C-H trifluoromethylthiolation

The first example of a practical and direct trifluoromethylthiolation reaction of unactivated aliphatic C-H bonds employs a silver-based reagent. The reaction is operationally simple, scalable, and proceeds under aqueous conditions in air. Furthermore, its broad scope and good functional-group compatibility were demonstrated by applying this method to the selective trifluoromethylthiolation of natural products and natural-product derivatives.

Regioselectivity in the ring opening of 2-phenyl-1,3-dioxan-2-yl radicals derived from cyclic benzylidene acetals and comparison with deoxygenation of a carbohydrate diol via its cyclic thionocarbonate

Ring-opening β-scission of monocyclic 2-phenyl-1,3-dioxan-2-yl radicals gives preferentially the more stabilised alkyl radical. However, analogous bicyclic radicals derived from two 4,6-O-benzylidene glucopyranosides afford primary radicals in preference to secondary radicals, a result that can be rationalised with the aid of DFT calculations. The report by Barton and Subramanian, that the opposite regioselectivity results from the tin hydride mediated reductive ring-opening of a corresponding glucosidic thionocarbonate, is shown to be in error.

Radical-chain redox rearrangement of cyclic benzylidene acetals to benzoate esters in the presence of thiols

Cyclic benzylidene acetals derived from 1,2- and 1,3-diols undergo an efficient ring-opening redox rearrangement to give benzoate esters in the presence of a peroxide initiator and a thiol, which acts as a polarity-reversal catalyst to promote the radical-chain reaction.

1-ACYL-3-SUBSTITUTED IMIDAZOLIUM SALTS AS HIGHLY REACTIVE ACYLATING AGENTS

1-Acylimidazoles could be highly activated for acylation by the quarternizing with benzyl halides. 1-Acyl-3-benzylimidazolium halides were powerful acylating agents.Alcohols, phenols, and amines were converted to the corresponding esters and amides in excellent yields under mild conditions.Keywords - 1-acyl-3-substituted imidazolium salts; acylating agents; 1-acylimidazoles; 1-acetyl-3-benzylimidazolium bromide; 1-benzoyl-3-benzylimidazolium bromide