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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
[Image: see text] 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 n...
| Autores principales: | , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2022
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9639068/ https://www.ncbi.nlm.nih.gov/pubmed/36283069 http://dx.doi.org/10.1021/acs.joc.2c01855 |
| _version_ | 1784825556926201856 |
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| author | Alvarez-Dorta, Dimitri León, Elisa I. Martín, Ángeles Kennedy, Alan R. Pérez-Martín, Inés Shankland, Kenneth Suárez, Ernesto |
| author_facet | Alvarez-Dorta, Dimitri León, Elisa I. Martín, Ángeles Kennedy, Alan R. Pérez-Martín, Inés Shankland, Kenneth Suárez, Ernesto |
| author_sort | Alvarez-Dorta, Dimitri |
| collection | PubMed |
| description | [Image: see text] 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. |
| format | Online Article Text |
| id | pubmed-9639068 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2022 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-96390682022-11-08 Regio- and Stereoselectivity of the Norrish–Yang Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State Photochemistry of Two Polymorphs Alvarez-Dorta, Dimitri León, Elisa I. Martín, Ángeles Kennedy, Alan R. Pérez-Martín, Inés Shankland, Kenneth Suárez, Ernesto J Org Chem [Image: see text] 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. American Chemical Society 2022-10-25 2022-11-04 /pmc/articles/PMC9639068/ /pubmed/36283069 http://dx.doi.org/10.1021/acs.joc.2c01855 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
| spellingShingle | Alvarez-Dorta, Dimitri León, Elisa I. Martín, Ángeles Kennedy, Alan R. Pérez-Martín, Inés Shankland, Kenneth Suárez, Ernesto Regio- and Stereoselectivity of the Norrish–Yang Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State Photochemistry of Two Polymorphs |
| title | Regio- and Stereoselectivity
of the Norrish–Yang
Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State
Photochemistry of Two Polymorphs |
| title_full | Regio- and Stereoselectivity
of the Norrish–Yang
Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State
Photochemistry of Two Polymorphs |
| title_fullStr | Regio- and Stereoselectivity
of the Norrish–Yang
Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State
Photochemistry of Two Polymorphs |
| title_full_unstemmed | Regio- and Stereoselectivity
of the Norrish–Yang
Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State
Photochemistry of Two Polymorphs |
| title_short | Regio- and Stereoselectivity
of the Norrish–Yang
Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State
Photochemistry of Two Polymorphs |
| title_sort | regio- and stereoselectivity
of the norrish–yang
photocyclization of dialkyl 1,2-diketones: solution versus solid state
photochemistry of two polymorphs |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9639068/ https://www.ncbi.nlm.nih.gov/pubmed/36283069 http://dx.doi.org/10.1021/acs.joc.2c01855 |
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