Ketene Di(2‐Methoxyethyl) Acetal

Kuryla, William C.; Hyre, John E.

doi:10.1002/0471264180.os047.24

Search citation statements

Order By: Relevance

Paper Sections

Select...

Results1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2011

Publication Types

Select...

Article1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

(1 citation statement)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Whereas ethyl vinyl ether was found to be unreactive toward diene 13 , ketene acetals 120 and 121 reacted slowly at reflux in dichloromethane (see Scheme ). In the case of 120 , IEDDA adduct 122 was isolated in 72% yield after 20 h of reaction.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 6H-Dibenzo[b,d]pyran-6-ones Using the Inverse Electron Demand Diels–Alder Reaction

et al. 2011

View full text Add to dashboard Cite

A set of coumarin-fused electron-deficient 1,3-dienes was synthesized, which differ in the nature of the electron-withdrawing group (EWG) at the terminus of the diene unit and (when EWG = CO(2)Me) the nature and position of substituents. These dienes reacted with the enamine derived from cyclopentanone and pyrrolidine to afford the corresponding cyclopenteno-fused 6H-dibenzo[b,d]pyran-6-ones, most likely via a domino inverse electron demand Diels-Alder (IEDDA)/elimination/transfer hydrogenation sequence. The parent diene (EWG = CO(2)Me, no substituents) was reacted with a range of electron-rich dienophiles (mostly enamines) to afford the corresponding 6H-dibenzo[b,d]pyran-6-ones or their nondehydrogenated precursors, which were aromatized upon treatment with a suitable oxidant. The enamines could either be synthesized prior to the reaction or generated in situ. The syntheses of 30 dibenzopyranones are reported.

show abstract

Section: Resultsmentioning

confidence: 99%