Regio- and Stereoselectivity of the Norrish–Yang Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State Photochemistry of Two Polymorphs

Regio- and Stereoselectivity of the Norrish–Yang Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State Photochemistry of Two Polymorphs

As shown by X-ray crystallography, crystals of 3β-acetoxy-16,17-seco-17,20-dioxopregn-5-ene-16-nitrile are dimorphic. The regioselectivity of the Norrish–Yang type II photocyclization under visible light of this steroidal 1,2-diketone, which bears primary, secondary, and tertiary nonequivalent abstractable γ-hydrogens, dramatically increases in the crystalline state of both polymorphs. X-ray crystallography and molecular mechanics calculations reveal crystal structure–solid state photochemistry relationships.

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Bibliographic Details
Main Authors: Álvarez-Dorta, Dimitri, León, Elisa I., Martín, Ángeles, Kennedy, Alan R., Pérez-Martín, Inés, Shankland, Kenneth, Suárez, Ernesto
Other Authors: Ministerio de Economía y Competitividad (España)
Format: artículo biblioteca
Language:English
Published: ACS Publications 2022-10-25
Subjects:Crystal structure, crystals, diffraction, irradiation, photocyclization,
Online Access:http://hdl.handle.net/10261/288760
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http://hdl.handle.net/10261/288760

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