Contents I. Introduction 415 II. Reaction Mechanism 416 III. Scope and Limitation of the Reaction 417 A. Alkyl Halides 418 B. Tricoordinate Phosphorus Reactant 420 C. Effectiveness of Catalysts 421 IV. Synthetic Applications 421 A. Synthesis of Phosphonates 421 B. Synthesis of Phosphinates 422 C. Synthesis of Tertiary Phosphine Oxides 423 D. Synthesis of Phosphonyl and Phosphinyl Halides 424 E. Other Synthetic Applications 424 V. Behaviour of Sulfur and Fluorine Analogues under Arbuzov Conditions 425
2‐Keto‐1,2,3,4‐tetrahydroquinoxaline I is rapidly oxidised to 2‐hydroxyquinoxaline II on reaction with cupric chloride. This is an oxidation‐reduction reaction in which the cupric chloride in the process is reduced to cuprous chloride. The latter instantaneously reacts with II forming an insoluble brick red complex. Compound II can be regenerated from the complex by treatment with alkali. The properties of this new complex are discussed.
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