95535-46-9Relevant academic research and scientific papers
Fluorescent and Nonfluorescent Aryl Vinyl Sulfones - Reagents Suitable for Protection and Detection of Thiol Functions
Horner, Leopold,Lindel, Hans
, p. 22 - 33 (2007/10/02)
The rate of the addition of primary, secondary, and tertiary thiols to aryl/alkyl vinyl sulfones 1 and 4-7 is investigated by competing reactions and by kinetics.The obtained acid stable 2-(alkyl-/arylthio)ethyl sulfones are cleaved by bases to give the starting material by rates corresponding to the rates of addition.Therefore, selective introduction and selective elimination of different (arylsulfonyl)ethyl protective groups in the same molecule is possible by using different kinetic steering factors. - Application of the fluorescent vinyl sulfones 5, 10, and 11 opens new fields for analysis and synthesis.SH-selective vinyl sulfones and thiophosphinic acid cyanides are "orthogonal" protective groups.
