NADH model studies. Part 2. Cationic hydrogenations using acridan derivatives as hindered NADH models
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 1273-1275
- https://doi.org/10.1039/p19860001273
Abstract
Various aryl alcohols (5), arylethylenes (6), and trityl ethers (7) are found to undergo smooth reduction in dichloromethane at room temperature when treated with an equimolar amount of the acridans (3) and trifluoroacetic acid. The limiting acidity value (H0) for the medium in which the compounds (3) are completely protonated and hence not suitable as NADH models was also determined spectrophotometrically. Kinetic studies of reduction of (5) with (3) in dilute sulphuric acid, or Hantzsch ester (2) in glacial acetic acid, indicated that during reduction steric hindrance is important in less acidic media whereas the reduction of cations performed with trifluoroacetic acid is not affected by steric factors.This publication has 3 references indexed in Scilit:
- Mechanisms of the primary acid modification reaction of reduced diphosphopyridine nucleotide modelsBiochemistry, 1968
- The biological conversion of 7-dehydrocholesterol into cholesterol and comments on the reduction of double bondsBiochemical Journal, 1968
- Acid-Catalyzed Addition of Water to 1,4-Dihydronicotinamide Derivatives*Biochemistry, 1963