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.
Original language | English |
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Pages (from-to) | 5656-5659 |
Number of pages | 4 |
Journal | Angewandte Chemie International Edition in English |
Volume | 59 |
Issue number | 14 |
DOIs | |
State | Published - 27 Mar 2020 |
Keywords
- carbocycles
- domino reactions
- pericyclic reactions
- photochemistry
- rearrangement