P-Toluenesulfonylazide

Product name:P-Toluenesulfonylazide

CAS NO: 941-55-9

Molecular formula: C7H7N3O2S

Molecular weight: 197.22

Product description:  A number of concurrent reactions of p-toluenesulfonyl azide-2-15N (I-3-15N) with the sodium salt of p-toluenesulfonamide were followed by 15N NMR. I-2-15N is formed as a result of a degenerate diazo transfer by I-3-15N to p-toluenesulfonamide anion. p-Toluenesulfonamide anion also reacts with 1-3-15N to give di-p-toluenesulfonamide and azide ion. The 15-N-labeled azide ion exchanges with I to give I-1-15N. I also reacts with azide ion, yielding dinitrogen and p-toluenesulfinate anion. The sulfinate salt reacts readily and reversibly with I to give 1,3-di-p-toluenesulfontriazene anion, which provides another pathway for interconversion of 1-3-15N and I-1-15N. The reaction of p-toluenesulfonyl azide with potassium azide-I-15N has been examined in toluene and dichloromethane by 15N NMR. In addition to azide-ion exchange leading to 1-1-15N and I-3-15N, the formation of 1-2-15N is indicated. Two mechanisms for this novel scrambling are proposed. Azide-ion metathesis involving reversible formation of an N-Pentazole derivative from I and azide ion, followed by azide exchange could account for the formation of 1-2-15N. Alternatively, a scrambling route involving the reversible addition of p-toluenesulfonylnitrene to 1-3-15N can be envisioned. The inhibition of scrambling in dichloromethane by addition of iodide ion suggests that a discrete p-toluenesulfonyl azide – azide ion intermediate is involved in any case.