Cleavage of S-S Bond by Nitric Oxide (NO) in the Presence of Oxygen. A Disproportionation Reaction of Two Disulfides.

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Disulfide bond was cleaved by a catalytic amount of nitric oxide in the presence of oxyge, which was confirmed by experiments employing two symmetrical disulfides. The reaction resulted in the formation of unsym-metrical disulfides in nearly 50% yields. The steric hindrance of alkyl disulfide slowed the reaction rate, and an electron-donating group on the aryl disulfide promoted the reaction. The substituent and S-nitrosothiol effects suggested that the reaction was initialized with an oxidative process by NO+.

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