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In organic chemistry, an allyl group is a substituent with the structural formula −CH 2 −HC=CH 2. It consists of a methylene bridge ( −CH 2 − ) attached to a vinyl group ( −CH=CH 2 ). [ 1 ] [ 2 ] The name is derived from the scientific name for garlic , Allium sativum .
The Tsuji–Trost reaction (also called the Trost allylic alkylation or allylic alkylation) is a palladium-catalysed substitution reaction involving a substrate that contains a leaving group in an allylic position. The palladium catalyst first coordinates with the allyl group and then undergoes oxidative addition, forming the π-allyl
An allylic rearrangement or allylic shift is an organic chemical reaction in which reaction at a center vicinal to a double bond causes the double bond to shift to an adjacent pair of atoms: It is encountered in both nucleophilic and electrophilic substitution , although it is usually suppressed relative to non-allylic substitution.
Allylic strain in an olefin. Allylic strain (also known as A 1,3 strain, 1,3-allylic strain, or A-strain) in organic chemistry is a type of strain energy resulting from the interaction between a substituent on one end of an olefin (a synonym for an alkene) with an allylic substituent on the other end. [1]
Allyl alcohol is produced commercially by the Olin and Shell corporations through the hydrolysis of allyl chloride: CH 2 =CHCH 2 Cl + NaOH → CH 2 =CHCH 2 OH + NaCl. Allyl alcohol can also be made by the rearrangement of propylene oxide, a reaction that is catalyzed by potassium alum at high temperature. The advantage of this method relative ...
Carbonyl allylation has been employed in the synthesis of polyketide natural products and other oxygenated molecules with a contiguous array of stereocenters. For example, allylstannanation of a threose-derived aldehyde affords the macrolide antascomicin B, which structurally resembles FK506 and rapamycin, and is a potent binder of FKBP12. [12]
The Mislow–Evans rearrangement is a name reaction in organic chemistry. It is named after Kurt Mislow who reported the prototypical reaction in 1966, [1] and David A. Evans who published further developments. [2] The reaction allows the formation of allylic alcohols from allylic sulfoxides in a 2,3-sigmatropic rearrangement. [3]
The Kharasch–Sosnovsky reaction is a method that involves using a copper or cobalt salt as a catalyst to oxidize olefins at the allylic position, subsequently condensing a peroxy ester (e.g. tert-Butyl peroxybenzoate) or a peroxide resulting in the formation of allylic benzoates or alcohols via radical oxidation. [1]