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Regio- and stereoselectivity of the Norrish−Yang photocyclization of Dialkyl 1,2-Diketones: solution versus solid state photochemistry of two polymorphS

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Alvarez-Dorta, D., Leon, E. I., Martin, A., Kennedy, A. R., Perez-Martin, I., Shankland, K. ORCID: https://orcid.org/0000-0001-6566-0155 and Suarez, E. (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

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To link to this item DOI: 10.1021/acs.joc.2c01855

Abstract/Summary

As shown by X-ray crystallography, crystals of 3βacetoxy-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.

Item Type:Article
Refereed:Yes
Divisions:Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Xray (CAF)
Life Sciences > School of Chemistry, Food and Pharmacy > School of Pharmacy > Pharmaceutics Research Group
ID Code:108542
Publisher:American Chemical Society
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