beta-Carotene (beta-Car) was chemically oxidized in a -2e(-) process using 2 mol equiv of NOSbF6 in a 4:1 ratio (v/v) of dichloromethane: acetonitrile to form the beta-carotene dication (beta-Car(2+)). Voltammetric monitoring of the chemical oxidation experiments over a range of temperatures indicated that the half-life of beta-Car(2+) was approximately 20 min at -60 degrees C, and approximately 1 min at -30 degrees C. alpha-Tocopherol (alpha-TOH) was chemically oxidized in a -2e(-)/-H+ process using 2 mol equiv of NOSbF6 to form the diamagnetic cation (alpha-TO+) which survives indefinitely at -60 degrees C in a 4:1 ratio (v/v) of dichloromethane:acetonitrile. Cyclic voltammetry experiments indicated that the oxidative peak potential for alpha-TOH was approximately +0.4 V more positive than the oxidative peak potential of beta-Car. When solutions of alpha-TO+/H+ (prepared by chemical oxidation of alpha-TOH with 2 NO+) were reacted with solutions containing equal molar amounts of beta-Car, voltammetric monitoring indicated that alpha-TOH was quantitatively regenerated and beta-Car(2+) was formed in high yield in a homogeneous two-electron transfer, according to the reaction alpha-TO+ + H+ + beta-Car -> alpha-TOH + beta-Car(2+).