In search of a method for the removal of carbobenzoxy groups from the nitrogen atoms in thyroxine-containing peptides, Harington (1) observed that hydrogen iodide (or, better, phosphonium iodide) in glacial acetic acid achieves the desired reaction, giving the amine hydriodide, benzyl iodide, and carbon dioxide.RNHCOOC7H7 + HI -> RNHrHI + C7H7I + C02 This reaction represents a non-hydrolytic cleavage and not, as claimed by several investigators (1, 2), a reduction process. Indeed hydrogen chloride (in anhydrous ethanol) eliminates the carbobenzoxy group in (N-carbobenzoxytyrosyl)tyrosine or carbobenzoxyglycine (3) and (in glacial acetic acid) cleaves ethyl carbamate to ammonium chloride, ethyl chloride, and carbon dioxide (4).The general application of this reaction especially to N-carbobenzoxy com-

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