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

Dimitri Alvarez-Dorta, Elisa I. León, Ángeles Martín, Alan R. Kennedy, Inés Pérez-Martín, Kenneth Shankland, Ernesto Suárez

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
Pages (from-to)14940-14947
Number of pages8
JournalJournal of Organic Chemistry
Volume87
Issue number21
Early online date25 Oct 2022
DOIs
Publication statusPublished - 4 Nov 2022

Keywords

  • regio- and stereoselectivity
  • Norrish−Yang photocyclization
  • dialkyl 1,2-diketones
  • solution
  • solid state phytochemistry
  • polymorphs

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