dietyyliazodikarbonaatti

Dietyyliazodikarbonaatti, often abbreviated as DEAD, is an organic compound with the chemical formula C6H14N2O2. It is a diazo compound and is characterized by the presence of two ethyl ester groups attached to a nitrogen-nitrogen double bond. DEAD is a highly reactive electrophilic reagent and is primarily used in organic synthesis as an oxidizing agent and a dienophile.

One of its most prominent applications is in the Mitsunobu reaction, where it facilitates the inversion of stereochemistry in alcohols during esterification or etherification. In this reaction, DEAD, along with triphenylphosphine, activates an alcohol, allowing for its displacement by a nucleophile with the opposite configuration. DEAD is also employed in various cyclization reactions and as a source of nitrogen in certain organic transformations. Due to its reactive nature, DEAD is typically handled with care. It is a pale yellow liquid and is often purchased and used as a solution in solvents like tetrahydrofuran or toluene to mitigate risks associated with its concentrated form. Its instability and potential for explosive decomposition under certain conditions necessitate careful storage and handling practices.