Free Radical Chain Reactions of [1.1.1]Propellane with Three-Coordinate Phosphorus Molecules. Evidence for the High Reactivity of the Bicyclo[1.1.1]pent-1-yl Radical

• Published in: Journal of the American Chemical Society Vol. 119; no. 6; pp. 1388 - 1399
• Main Authors: Dockery, Kevin P, Bentrude, Wesley G
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 12.02.1997; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; C-13; MECHANISM; RESONANCE; AMINO; CHEMISTRY; TINKERTOY CONSTRUCTION SET; PARENT HYDROCARBONS; BENZYL PHOSPHITES; ABSOLUTE RATE CONSTANTS; STAFFANES

Three-substituted bicyclo[1.1.1]pent-1-yl radicals (5), generated from additions of radicals to [1.1.1]propellane (1), are found to have high propensities to react with three-coordinate phosphorus molecules. For example, the 3-ethylbicyclo[1.1.1]pent-1-yl radical (5d) reacts with (EtO)3P in a free-r...