Regio- and Stereoselectivity of the Norrish–Yang Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State Photochemistry of Two Polymorphs

Álvarez-Dorta, Dimitri; León, Elisa I.; Martín, Ángeles; Kennedy, Alan R.; Pérez-Martín, Inés; Shankland, Kenneth; Suárez, Ernesto; Ministerio de Economía y Competitividad (España)

Regio- and Stereoselectivity of the Norrish–Yang Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State Photochemistry of Two Polymorphs

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.

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Bibliographic Details
Main Authors:	Álvarez-Dorta, Dimitri, León, Elisa I., Martín, Ángeles, Kennedy, Alan R., Pérez-Martín, Inés, Shankland, Kenneth, Suárez, Ernesto
Other Authors:	Ministerio de Economía y Competitividad (España)
Format:	artículo biblioteca
Language:	English
Published:	ACS Publications 2022-10-25
Subjects:	Crystal structure, crystals, diffraction, irradiation, photocyclization,
Online Access:	http://hdl.handle.net/10261/288760
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spelling	dig-ipna-es-10261-2887602023-02-09T11:54:32Z Regio- and Stereoselectivity of the Norrish–Yang Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State Photochemistry of Two Polymorphs Álvarez-Dorta, Dimitri León, Elisa I. Martín, Ángeles Kennedy, Alan R. Pérez-Martín, Inés Shankland, Kenneth Suárez, Ernesto Ministerio de Economía y Competitividad (España) CSIC - Unidad de Recursos de Información Científica para la Investigación (URICI) Crystal structure crystals diffraction irradiation photocyclization 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. Financial support by the Investigation Programs of the Ministerio de Economía y Competitividad (CTQ2010-18244) is acknowledged. D.A.-D. thanks the Ministerio de Economía y Competitividad for a fellowship. The authors acknowledge support of the publication fee by the CSIC Open Access Publication Support Initiative through its Unit of Information Resources for Research (URICI). Peer reviewed 2023-02-09T11:54:32Z 2023-02-09T11:54:32Z 2022-10-25 artículo Journal of Organic Chemistry, 87(21), 14940–14947, 1-8 (2022) 0022-3263 http://hdl.handle.net/10261/288760 10.1021/acs.joc.2c01855 1520-6904 en #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/MICINN//CTQ2010-18244/ES/APLICACIONES SINTETICAS DE LOS PROCESOS DE TRANSFERENCIA INTRAMOLECULAR DE HIDROGENO EN SISTEMAS DE CARBOHIDRATOS. OBTENCION DE NUEVOS SINTONES QUIRALES/ Publisher's version https://doi.org/10.1021/acs.joc.2c01855 Sí open ACS Publications
institution	IPNA ES
collection	DSpace
country	España
countrycode	ES
component	Bibliográfico
access	En linea
databasecode	dig-ipna-es
tag	biblioteca
region	Europa del Sur
libraryname	Biblioteca del IPNA España
language	English
topic	Crystal structure crystals diffraction irradiation photocyclization Crystal structure crystals diffraction irradiation photocyclization
spellingShingle	Crystal structure crystals diffraction irradiation photocyclization Crystal structure crystals diffraction irradiation photocyclization Álvarez-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
description	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.
author2	Ministerio de Economía y Competitividad (España)
author_facet	Ministerio de Economía y Competitividad (España) Álvarez-Dorta, Dimitri León, Elisa I. Martín, Ángeles Kennedy, Alan R. Pérez-Martín, Inés Shankland, Kenneth Suárez, Ernesto
format	artículo
topic_facet	Crystal structure crystals diffraction irradiation photocyclization
author	Álvarez-Dorta, Dimitri León, Elisa I. Martín, Ángeles Kennedy, Alan R. Pérez-Martín, Inés Shankland, Kenneth Suárez, Ernesto
author_sort	Álvarez-Dorta, Dimitri
title	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_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_sort	regio- and stereoselectivity of the norrish–yang photocyclization of dialkyl 1,2-diketones: solution versus solid state photochemistry of two polymorphs
publisher	ACS Publications
publishDate	2022-10-25
url	http://hdl.handle.net/10261/288760
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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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