Organic Reactions 2024
DOI: 10.1002/0471264180.or115.01
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(4+3) Cycloadditions of Allylic and Related Cations

Michael Harmata,
Jianzhuo Tu,
Madison M. Clark

Abstract: The reaction of allylic cations with 1,3‐dienes is formally equivalent to the Diels–Alder reaction but leads to seven‐membered rings. An allylic cation contains 2 pi electrons, and is thus precisely analogous to an alkene and, like the latter, can function as a dienophile. The substituent at the central carbon of the allylic cation serves to terminate the reaction. Most often, this substituent is an oxyanion or a silyl ether, but other groups have been used. These (4+3) cycloadditions can proceed via mechanism… Show more

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