The present research has demonstrated that selective C−S bond cleavages of dibenzothiophene and its derivatives are feasible by thia‐Baeyer–Villiger type oxidation, i. e. the oxygen insertion process within a sulfoxide‐carbon linkage, in the presence of porphyrin iron (III) and by ultraviolet irradiation originating from sunlight, high pressure Hg‐lamp or residentially germicidal ultraviolet lamp under very mild conditions. This reaction with tert‐butylhydroperoxide at 30.0 °C leads to dibenzo[1,2]oxathiin‐6‐oxide (PBS) in 83.2 % isolated yield or its hydrated products, 2‐(2‐hydroxyphenyl)‐benzenesulfinic derivatives (HPBS) in near 100 % yield based HPLC data. PBS and HPBS are a type of biological products detected on the C−S bond cleavage step through various oxidative biodesulfurization (OBDS) pathways, and are useful synthetic intermediates and fine chemicals. These observations may contribute on understanding delicately molecular aspect of OBDS in the photosynthesis system, expanding the C‐S cleavage chemistry of S‐heterocyclic compounds and approaching toward biomemic desulfurization with respect to converting sulfur contaminants to chemically beneficial blocks as needed and performing under the ambient conditions.

中文翻译：

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二苯并噻吩亚砜衍生物的独特Thia-Baeyer-Villiger型氧化

本研究表明，在存在卟啉铁（III）和铁（III）的情况下，通过噻吩-拜耳-维利格型氧化，即亚砜-碳键内的氧插入过程，二苯并噻吩及其衍生物的选择性C-S键裂解是可行的。通过在非常温和的条件下从日光，高压汞灯或民用紫外线杀菌灯发出的紫外线照射。在30.0°C下与叔丁基氢过氧化物的反应可生成83.2％的分离产率的二苯并[1,2]草酰氧-6-氧化物（PBS）或它的水合产物，其中的2-（2-羟基苯基）-苯亚砜衍生物（HPBS）基于HPLC数据的收率接近100％。PBS和HPBS是通过各种氧化生物脱硫（OBDS）途径在CS键断裂步骤上检测到的一种生物产物，并且是有用的合成中间体和精细化学品。这些观察结果可能有助于深入了解光合作用系统中OBDS的分子方面，扩展S杂环化合物的C-S裂解化学，并朝着生物组学脱硫的方向发展，以便根据需要将硫污染物转化为化学有益的嵌段并在环境条件下运行条件。