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

2013年12月2日 · In allylic bromination reactions, the C-H bond of an allylic carbon breaks, and a new C-Br bond is formed. This reaction sometimes occurs with allylic rearrangement. That is, the new C-Br bond forms on the end carbon of the pi-bond, and the pi bond moves over such that the original sp 3 -hybridized C-H carbon becomes an alkenyl carbon.

The general pathway for allylation with allylborons is one that occurs with allylic rearrangement. Like most allylmetal systems, allylborons have the potential to undergo reaction at either their α- or γ-position.

Ferrier rearrangement is a chemical process in which 1, 2-unsaturated carbohydrates (glycals) undergo Lewis acid catalysed allylic rearrangement with nucleophilic displacement to 2, 3-unsaturated sugars. Ferrier reactions have proven helpful in piecing together synthetic approaches to complex molecules for research and industry.

Unlike most organic azides, allylic azides can spontaneously rearrange to form a mixture of isomers. This rearrangement has been named the Winstein rearrangement. Using allylic azides can result in low yields and azide racemization in some …

2023年8月18日 · We describe here a valuable alternative to the synthesis of allylic alcohols via 1,2-metallate rearrangement. In this work, various vinyl boronic esters with different functional groups have been applied in the Hoppe–Matteson–Aggarwal reaction.

2024年6月7日 · We report a photochemical method for the semipinacol rearrangement of unactivated allylic alcohols. Aliphatic as well as aromatic groups participate as migrating groups, yielding a variety of α,α-disubstituted ketones.

2024年12月23日 · A mechanistic study of the isothiourea-catalyzed enantioselective [2,3]-rearrangement of allylic ammonium ylides is described. Reaction kinetic analyses using 19F NMR and d. functional theory computations have elucidated a reaction profile and allowed identification of the catalyst resting state and turnover-rate limiting step.

2025年1月10日 · The Pd-catalyzed asymmetric hydrogenolysis rearrangement of allylic acetates using (s-Bu)3BHK has been described, achieving the synthesis of axially chiral alkylidene cycloalkanes with excellent enantioselectivities (up to 99% ee) and a wide substrate scope (30 examples of cyclohexanes and cyclobutanes).

6 天之前 · Amides are among the most important functional groups in both nature and laboratory settings 1,2,3,4,5.Amides are commonly used as fine chemicals and synthetic building blocks 6,7,8,9,10,11,12 ...