What is Frankland reagent?

As of my last update in September 2021, Frankland reagent, also known as "Zinc alkyls" or "Frankland's reagent," is a chemical compound used in organic chemistry. It is named after the English chemist Sir Edward Frankland, who first prepared and studied these compounds in the mid-19th century.

Frankland reagent is an organometallic compound that contains a zinc-carbon bond. It is typically represented by the general formula R-Zn-X, where R is an alkyl or aryl group and X is a halogen atom (such as chlorine, bromine, or iodine). The most common form of Frankland reagent is diethylzinc (Et2Zn).

Frankland reagent is particularly useful in organic synthesis as it serves as a source of carbon-centered radicals or carbanions, which can be used to create carbon-carbon bonds. It is a strong nucleophile and can participate in various reactions, such as the Frankland reaction, where it reacts with alkyl halides to form higher alkanes.

The reactivity and usefulness of Frankland reagent stem from the high polarity of the zinc-carbon bond, making it susceptible to nucleophilic attack. However, it is important to handle Frankland reagent with care, as it is pyrophoric, meaning it can ignite spontaneously in the presence of air or moisture.

Please keep in mind that there may have been further developments or research on this topic beyond my last update, so it's always a good idea to consult more recent sources for the latest information.