Accessibility navigation


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

Alvarez-Dorta, D., Leon, E. I., Martin, A., Kennedy, A. R., Perez-Martin, I., Shankland, K. 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

[img]
Preview
Text (Open access) - Published Version
· Available under License Creative Commons Attribution.
· Please see our End User Agreement before downloading.

1MB

It is advisable to refer to the publisher's version if you intend to cite from this work. See Guidance on citing.

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

Downloads

Downloads per month over past year

University Staff: Request a correction | Centaur Editors: Update this record

Page navigation