Dimethylmalonyltrialkylphosphoranes: New General Reagents for Esterification Reactions Allowing Controlled Inversion or Retention of Configuration on Chiral Alcohols.

Abstract

Alcohols. -Dimethylmalonyltrialkylphosphoranes are found to be efficient promoters for the condensation of carboxylic acids with alcohols. The reaction with chiral secondary alcohols leads to esters with retention or inversion of configuration depending on solvent, steric and electronic nature of acid, and steric nature of phosphorane. -(MCNULTY*, J.; CAPRETTA, A.; LARITCHEV, V.; DYCK, J.; ROBERTSON, A. J.; J. Org. Chem. 68 (2003) 4, 1597-1600; Dep. Chem., Brock Univ., St. Catharines, Ont. L2S 3A1, Can.; Eng.) -Jannicke 26-100 2003 Carboxylic acid esters

Novel C‐C Bond Cleavage from Arylacetonitriles in Alcohols to Aryl Carboxylic Esters using Potassium Iodide and Catalytic Amount of Samarium

“…[12] More recently, many new methods to prepare aryl carboxylic esters were described, for example, (a) direct conversion of aldehydes in alcoholic solvents to their corresponding ester products utilizing oxone or peroxovanadium as the oxidant; [13,14] (b) conversion of electron-deficient aryl alkyl ketones to aryl esters in methanol; [15] (c) condensation reaction of carboxylic acids with alcohols to provide esters promoted by dimethylmalonyltrialkylphos phoranes. [16] Herein we report a novel C-C bond cleavage from arylacetonitriles in alcohols to their corresponding aryl carboxylic esters using potassium iodide and a catalytic amount of samarium. Reaction steps are outlined in Scheme 1.…”

Assessing Carbazole Derivatives as Single-Electron Photoreductants

“…Spectra were in accordance with those described in the literature. 30 Method B was also used with methyl 3-bromobenzoate (7e, 0.086 g, 0.40 mmol) and carbazole 3a. The calibrated yield was determined by the ratio of product to dodecane to be >99%.…”