[2+2]‐Cycloadditionen von Allylkationen

The reaction of ketenes 1a or 1b with diene 2 in the presence of trifluoromethanesulfonic acid providing the cycloheptadienones 5a and 5b constitutes the first example of an acid‐induced ketene/diene «cycloaddition». The thermal [2 + 2] cycloadducts, bicyclo[3.2.0]hept‐2‐en‐6‐ones 9, are not intermediates in the acid‐catalyzed reaction since they rearrange under acidic conditions to the tetralinone derivatives 10. The acid‐catalyzed «cycloaddition» was mechanistically investigated and the scope of the reaction explored.

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ChemInform Abstract: (2+2) CYCLOADDITIONS OF ALLYL CATIONS

Klein¹,

Freyberger²,

Mayr³

1983

Chemischer Informationsdienst

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[2+2]‐Cycloadditionen von Allylkationen

Abstract: Behandelt man ein Gemisch aus 4-Chlor-2-methyl-2-penten 1 und 2,3-Dimethyl-2-buten 2 mit ZinkchloridEther bei -78 °C, erhalt man das Cydobutan-Derivat 3 Pal I·) Priv.-Doz.

Cited by 7 publications

References 10 publications

Lewis‐Säure‐katalysierte Additionen 1,3‐Alkyl‐substituierter Allylchloride an Alkene

Lewis‐Säure‐katalysierte Additionen 1,3‐Alkyl‐substituierter Allylchloride an Alkene

Acid‐Induced Stereoselective Formation of 3,5‐Cycloheptadien‐1‐ones from Ketenes and Dienes

ChemInform Abstract: (2+2) CYCLOADDITIONS OF ALLYL CATIONS

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