Development of a Vinylated Cyclic Allene: A Fleeting Strained Diene for the Diels-Alder Reaction.

ABSTRACT: Fleeting molecules possessing strained multiple bonds are important components in organic synthesis due to their ability to undergo various chemical reactions driven by the release of strain energy. Although the use of strained π-bonds as 2π components, represented by dienophiles in Diels-Alder reactions, has been well studied, "the strained diene (4π component) approach" for molecular construction remains underexplored. Herein, we report the design of a vinyl cyclic allene (1-vinyl-1,2-cyclohexadiene) as a highly reactive strained diene and the development of its Diels-Alder reactions. Experimental and computational studies of vinyl cyclic allenes revealed that this diene system undergoes cycloaddition with dienophiles regio- and stereoselectively under mild reaction conditions. These stu

SUBMITTER: Mizoguchi H 

PROVIDER: S-EPMC12338423 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature