Organolithium reagentIn organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers.
AlkyneAcetylene Propyne 1-Butyne In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula . Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to , known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.
AcetylideIn organometallic chemistry, acetylide refers to chemical compounds with the chemical formulas and , where M is a metal. The term is used loosely and can refer to substituted acetylides having the general structure (where R is an organic side chain). Acetylides are reagents in organic synthesis. The calcium acetylide commonly called calcium carbide is a major compound of commerce. Alkali metal and alkaline earth metal acetylides of the general formula MC≡CM are salt-like Zintl phase compounds, containing C22− ions.
N-Butyllithiumn-Butyllithium C4H9Li (abbreviated n-BuLi) is an organolithium reagent. It is widely used as a polymerization initiator in the production of elastomers such as polybutadiene or styrene-butadiene-styrene (SBS). Also, it is broadly employed as a strong base (superbase) in the synthesis of organic compounds as in the pharmaceutical industry. Butyllithium is commercially available as solutions (15%, 25%, 1.5 M, 2 M, 2.5 M, 10 M, etc.) in alkanes such as pentane, hexanes, and heptanes.
Sonogashira couplingThe Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vinyl halide. R1: aryl or vinyl R2: arbitrary X: I, Br, Cl or OTf The Sonogashira cross-coupling reaction has been employed in a wide variety of areas, due to its usefulness in the formation of carbon–carbon bonds.
Metal–halogen exchangeIn organometallic chemistry, metal–halogen exchange is a fundamental reaction that converts an organic halide into an organometallic product. The reaction commonly involves the use of electropositive metals (Li, Na, Mg) and organochlorides, bromides, and iodides. Particularly well-developed is the use of metal–halogen exchange for the preparation of organolithium compounds. Two kinds of lithium–halogen exchange can be considered: reactions involving organolithium compounds and reactions involving lithium metal.
DiethylzincDiethylzinc (C2H5)2Zn, or DEZ, is a highly pyrophoric and reactive organozinc compound consisting of a zinc center bound to two ethyl groups. This colourless liquid is an important reagent in organic chemistry. It is available commercially as a solution in hexanes, heptane, or toluene, or as a pure liquid. Edward Frankland first reported the compound in 1848 from zinc and ethyl iodide, the first organozinc compound discovered. He improved the synthesis by using diethyl mercury as starting material.
AllenesIn organic chemistry, allenes are organic compounds in which one carbon atom has double bonds with each of its two adjacent carbon atoms (, where R is H or some organyl group). Allenes are classified as cumulated dienes. The parent compound of this class is propadiene (), which is itself also called allene. An group of the structure is called allenyl, where R is H or some alkyl group. Compounds with an allene-type structure but with more than three carbon atoms are members of a larger class of compounds called cumulenes with bonding.
AlkynylationIn organic chemistry, alkynylation is an addition reaction in which a terminal alkyne () is added to a carbonyl group () to form an α-alkynyl alcohol (). When the acetylide is formed from acetylene (), the reaction gives an α-ethynyl alcohol. This process is often referred to as ethynylation. Such processes often involve metal acetylide intermediates. The principal reaction of interest involves the addition of the acetylene () to a ketone () or aldehyde (): RR'C=O + HC#CR'' -> RR'C(OH)C#CR'' The reaction proceeds with retention of the triple bond.
Elimination reactionAn elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1CB, exists.
