Tandem cheletropic additions of sulfur dioxide to [2.2.2]hericene. The ‘barrelene effect’

The Diels‐Alder cycloadditions of facially dissymmetric maleic anhydride 1 with facially nonequivalent exocyclic 1,3‐butadienes(dimethylidenebicyclo[2.2.2]octene 3 and 2,3,5,6‐tetramethylidenebicyclo[2.2.2]‐octene (4)) were investigated. In each cycloaddition, the reaction occurred via the course in which 1 added exclusively by its syn‐face (same face as the etheno‐bridge) onto either π‐face of the exocyclic 1,3‐butadiene systems to produce only two of the four possible stereoisomeric monocycloadducts (8a/8b and 9a/9b). In the Diels‐Alder cycloaddition of 1 with bis‐exocyclic butadiene 4, however, both monocycloadducts 9a and 9b underwent subsequent cycloaddition with distinctive facial selectivity to produce the Cs‐symmetric bis‐cyclohexanobarrelene 10a as only bis‐cycloadduct.

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Tandem cheletropic additions of sulfur dioxide to [2.2.2]hericene. The ‘barrelene effect’

Cited by 5 publications

References 60 publications

Appendix to ‘Synthesis of Open‐Chain Sulfones’

Appendix to ‘Synthesis of Open‐Chain Sulfones’

ChemInform Abstract: Tandem Cheletropic Additions of Sulfur Dioxide to (2.2.2)Hericene. The “Barrelene Effect”.

Stereoselectivity in the Diels‐Alder Cycloadditions of a Facially Dissymmetric Bicyclo[2.2.2]octadiene‐Grafted Maleic Anhydride with Exocyclic Butadienes. Unexpected Facial Selectivity in the Cycloaddition with 2,3,5,6‐tetramethylidenebicyclo[2.2.2]octene

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