title: Comparison of the reactivity of β-thiolactones and β-lactones toward ring-opening by thiols and amines.
abstract: An investigation into the comparative reactivity of simple β-lactones and β-thiolactones toward a thiol and a primary amine is reported. A simple 3-mercaptomethyl-2-oxetanone is found to undergo rearrangement in the presence of aqueous base to give the corresponding thietane-3-carboxylic acid rather than the 3-hydroxymethyl-2-thietanone. Implications for the use of β-thiolactones in bioorganic and medicinal chemistry are discussed.
authors: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif-sur-Yvette, France.
authors: Amandine
authors: A
authors: Noel
authors: Bernard
authors: B
authors: Delpech
authors: David
authors: D
authors: Crich
mesh_terms: D000588:Amines / Q000737:chemistry*; D003500:Cyclization; D007700:Kinetics; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000588:Amines; D007783:Lactones; D013438:Sulfhydryl Compounds