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- Title
Complex Carbocyclic Skeletons from Aryl Ketones through a Three‐Photon Cascade Reaction.
- Authors
Næsborg, Line; Jandl, Christian; Zech, Andreas; Bach, Thorsten
- Abstract
Starting from readily available 7‐substituted 1‐indanones, products with a tetracyclo[5.3.1.01,704,11]undec‐2‐ene skeleton were obtained upon irradiation at λ=350 nm (eight examples, 49–67 % yield). The assembly of the structurally complex carbon framework proceeds in a three‐photon process comprising an ortho photocycloaddition, a disrotatory [4π] photocyclization, and a di‐π‐methane rearrangement. The flat aromatic core of the starting material is converted into a functionalized polycyclic hydrocarbon with exit vectors in three dimensions. Ring opening reactions at the central cyclopropane ring were explored, which enable the preparation of tricyclo[5.3.1.04,11]undec‐2‐enes and of tricyclo[6.2.1.01,5]undecanes.
- Subjects
KETONES; SKELETON; PHOTOCYCLOADDITION; PHOTOCYCLIZATION; CORE materials; METHANE as fuel
- Publication
Angewandte Chemie, 2020, Vol 132, Issue 14, p5705
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201915731