区域和立体选择性的 Norrish-Yang 光环化反应的二烷基 1,2-二酮：两种多晶型物的溶液态和固态光化学。
Regio- and Stereoselectivity of the Norrish-Yang Photocyclization of Dialkyl 1,2-Diketones: Solution versus Solid State Photochemistry of Two Polymorphs.
机构信息
Síntesis de Productos Naturales, Instituto de Productos Naturales y Agrobiología del CSIC, Avda. Astrofísico Francisco Sánchez 3, 38206 La Laguna, Tenerife, Spain.
WestCHEM Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow G1 1XL, Scotland, United Kingdom.
出版信息
J Org Chem. 2022 Nov 4;87(21):14940-14947. doi: 10.1021/acs.joc.2c01855. Epub 2022 Oct 25.
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.
X 射线晶体学表明，3β-乙酰氧基-16,17-断孕-17,20-二氧代-5-烯-16-腈的晶体为二态。这种甾体 1,2-二酮带有伯、仲和叔不等价的可提取 γ-氢，在两种多晶型物的晶态下，Norrish-Yang 型 II 光环化的区域选择性在可见光下显著增加。X 射线晶体学和分子力学计算揭示了晶体结构-固态光化学关系。
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