Propargylic alcohols migration reaction

A mechanistically relevant dimerization of the propargyl alcohol derivative 69 resulting in 70 was also promoted by a cationic complex 68 (Scheme 4.25) [58]. The reaction was considered to start with the regioselective formation of the ruthena-cyclopentadiene 71 from 68 and 69, and the subsequent migration of the hydroxy... 

A few examples of vinylic to aryl rhodium migration have also been observed. One such example was discovered independently by two groups almost at the same time [77,78], In this reaction, aryl propargyl alcohols undergo a rhodium-catalyzed isomerization to furnish indanone products (Table 12). The reaction proceeds by a fairly complicated mechanism shown in Scheme 19. Thus, after base-promoted ligand... 

The carbolithiation- N C aryl migration sequence was performed in TH F, with and without the addition of DMPU, followed by the carbamate cleavage leading to highly substituted propargyl alcohols 47. When the enyne 48 was treated with n-BuLi in toluene without the addition of DMPU, allene products were observed after the protonation step (Scheme 10.16). The addition of (—)-sparteine and carrying out the reaction at —78 °C led to the product 49 as a racemic mixture or at best with moderate enantiomeric excess. 

Olefin migration Oxidation of alcohols Passerini reaction Pauson-Khand reaction Pinacol cross-coupling Pinner reaction Polymerization of olefins Prins reaction Propargylation Radical addition Radical cyclization Radical substitution Reduction... 

The reactions of allenyl and propargyl derivatives of boron, silicon or tin with carbonyl compounds or acetals take place with double-bond migration (Se reactions). Therefore, allenyl derivatives will lead to homopropargyl alcohols and propargyl analogs to allenyl alcohols. 

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