Regio- and stereoselectivity of the Norrish-Yang photocyclization of dialkyl 1,2- diketones. Solution versus solid state photochemistry of two polymorphs

Alvarez-Dorta, Dimitri and León, Elisa I. and Martín, Ángeles and Kennedy, Alan R. and Pérez-Martín, Inés and Shankland, Kenneth and Suárez, Ernesto (2022) Regio- and stereoselectivity of the Norrish-Yang photocyclization of dialkyl 1,2- diketones. Solution versus solid state photochemistry of two polymorphs. Journal of Organic Chemistry, 87 (21). pp. 14940-14947. ISSN 0022-3263 (https://doi.org/10.1021/acs.joc.2c01855)

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Abstract

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.

ORCID iDs

Alvarez-Dorta, Dimitri, León, Elisa I., Martín, Ángeles, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Pérez-Martín, Inés, Shankland, Kenneth and Suárez, Ernesto;
  • Item type:Article
    ID code:83037
    Dates:
    Date
    Event
    4 November 2022
    Published
    25 October 2022
    Published Online
    25 October 2022
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:02 Nov 2022 13:54
    Last modified:11 Nov 2024 13:40
    URI:https://strathprints.strath.ac.uk/id/eprint/83037
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