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Acrotyl group is anorganicfunctional group with the formulaRCH2CH=CHCH3.[1] Systematically, it is called a but-2-en-1-yl group and exhibitsgeometric isomerism, being eithercis (Z) ortrans (E). There are many simple compounds in which the crotyl group forms base carbon chain:crotyl alcohol,crotonaldehyde,crotonic acid, andcrotyl acrylate are examples.
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Crotylate (crotyl anions) can be synthesised from2-butene (either isomer): this reaction must be performed in the presence oforganometallic reagents, as abase, usuallyalkyllithium, or anyalkylates ofs-block metals, in a solvent, typicallyTHF, and at low temperatures, generally below -20 °C. The negative charge is delocalised over three of the carbon atoms of the crotylate group and there is resonance between the two possible delocalised forms (one for each terminal carbon).
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Crotylation readily occurs withalkoxyboronates to form crotylboronates.
Crotylboronates are useful reagents in the formation of crotyl alcohols. They react with the acidic protons ofaldehydes to form alcohols. The mechanism involves a six-membered ring involving the carbonyl oxygen and boron in a chair-like structure. Such reactions are highlydiastereoselective.