iodocarbene

Iodocarbene is a neutral, highly reactive species with the chemical formula CHI. It is a halocarbene containing iodine. Like other carbenes, iodocarbene possesses a divalent carbon atom with six valence electrons, making it electron-deficient and prone to addition reactions. It is typically generated in situ due to its instability.

Common methods for generating iodocarbene involve the decomposition of precursors such as iodoform (CHI3) or diaziodoiodomethane (ICN2). For instance, treatment of iodoform with a strong base can lead to the abstraction of a proton, followed by the elimination of two iodide ions to form iodocarbene. Another route involves the thermal decomposition of diazo compounds containing iodine.

Iodocarbene readily participates in various chemical transformations. One of its characteristic reactions is insertion into carbon-hydrogen bonds, although this is often less facile than with other halocarbenes. It can also add to carbon-carbon double bonds to form cyclopropane derivatives. Due to the relatively weak carbon-iodine bond, iodocarbene is a potent electrophile. Its transient nature and high reactivity make it a subject of study in organic synthesis and reaction mechanism investigations, rather than a commonly used reagent in standard laboratory procedures.