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Isomerizations of Propargyl 3-Acylpropiolates via Reactive Allenes.

ABSTRACT: Thermal isomerizations of various propargyl 3-acylpropiolates are described. Many result in the formation of 3-acylbutenolides. These reactions appear to proceed through intermediate 2,3-dehydropyrans (strained cyclic allenes), which then isomerize in a previously unobserved fashion. Competitive processes that provide additional mechanistic insights are also described.

SUBMITTER: Wang Y 

PROVIDER: S-EPMC6400065 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

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Isomerizations of Propargyl 3-Acylpropiolates via Reactive Allenes.

Wang Yuanxian Y   Hoye Thomas R TR  

Organic letters 20180712 15

Thermal isomerizations of various propargyl 3-acylpropiolates are described. Many result in the formation of 3-acylbutenolides. These reactions appear to proceed through intermediate 2,3-dehydropyrans (strained cyclic allenes), which then isomerize in a previously unobserved fashion. Competitive processes that provide additional mechanistic insights are also described. ...[more]

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