tert-Butyl nitrite

Description

tert-Butyl nitrite is a common reagent used for diazotization, typically for Sandmeyer reactions. Isoamyl nitrite is used for similar purposes.

The Uses of tert-Butyl nitrite

To ACN (350 mL) at RT was added CuBr2 (67 g, 300 mmol). The mixture was cooled to 0-5 C and was treated dropwise with t-BuONO (72.5 mL, 535 mmol). The mixture was stirred for 5 min, then was added the SM (35 g, 238 mmol). The reaction was stirred at RT for 2 h. EtOAc (525 mL) was added to the mixture and the reaction was quenched with 10% aq NH4Cl (350 mL) and 2% aq NH3 (175 mL). The layers were separated and the aq layer was extracted with EtOAc. The combined organics were dried and concentrated. The resulting material was purified by silica gel chromatography (eluting with 5% EtOAc/hexane) to provide the product as a yellow solid. [35 g, 70%]

The Uses of tert-Butyl nitrite

tert-Butyl nitrite is employed as a reagent for diazotization and nitrosation of alcohols, thiols, amines and cycloalkanes. It plays an important role in photocatalyzed conversion of aryl and heteroarylamines to selenides. It finds application in the preparation of aryl azides from aryl amines. It is also useful for radical multifunctionalization reactions of aliphatic alkenes and source of nitric oxide.