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 abstr...

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Bibliographic Details
Authors: Álvarez-Dorta, Dimitri, León, Elisa I., Martín, Ángeles, Kennedy, Alan R., Pérez-Martín, Inés, Shankland, Kenneth, Suárez, Ernesto
Format: article
Status:Published version
Publication Date:2022
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/288760
Online Access:http://hdl.handle.net/10261/288760
Access Level:Open access
Keyword:Crystal structure
crystals
Diffraction
irradiation
photocyclization
Description
Summary: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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