Publication

A regio- and stereocontrolled access to 2,4-dienols by amide/alcoholate-promoted ring-opening of dihydropyrans

Manfred Schlosser
1985
Journal Articles

Abstract

Dihydropyrans I (R = R1 = H, R2 = H, Me, CH2CH2CH:CMe2; R = Me, CH2CHMe2, R1 = H, R2 = Me; R = R2 = H, R1 = CH:CMe2), when treated with LiN(CHMe2)2-KOCMe3, underwent smooth ring cleavage through b-elimination to give dienols (Z)-HOCHRCR1:CR2CH:CH2. Methylenetetrahydropyrans II (R3 = Me, CH2CHMe2) gave HOCHR3CH2C(CH:CH2):CH2, while II (R3 = H) gave (E)-HOCH2CH:CMeCH:CH2. Other cyclic or acyclic homoallylic ethers reacted similarly. [on SciFinder (R)]

Official source

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Manfred Schlosser
1985
Journal Articles

Abstract

Official source

Related concepts (10)

Polycarbonate

Polycarbonates (PC) are a group of thermoplastic polymers containing carbonate groups in their chemical structures. Polycarbonates used in engineering are strong, tough materials, and some grades are optically transparent. They are easily worked, molded, and thermoformed. Because of these properties, polycarbonates find many applications. Polycarbonates do not have a unique resin identification code (RIC) and are identified as "Other", 7 on the RIC list. Products made from polycarbonate can contain the precursor monomer bisphenol A (BPA).

Beta-Hydride elimination

β-Hydride elimination is a reaction in which an alkyl group bonded to a metal centre is converted into the corresponding metal-bonded hydride and an alkene. The alkyl must have hydrogens on the β-carbon. For instance butyl groups can undergo this reaction but methyl groups cannot. The metal complex must have an empty (or vacant) site cis to the alkyl group for this reaction to occur. Moreover, for facile cleavage of the C–H bond, a d electron pair is needed for donation into the σ* orbital of the C–H bond.

Elimination reaction

An 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.