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Peroxides As "switches" Of Dialkyl H-phosphonate: Two Mild And Metal-free Methods For Preparation Of 2-acylbenzothiazoles And Dialkyl Benzothiazol-2-ylphosphonates.

X. Chen, X. Li, L. Qu, Yu-chun Tang, Wen-Peng Mai, Donghui Wei, Wen-Zhu Bi, Likun Duan, Kai Sun, J. Chen, Dian-Dian Ke, Y. Zhao
Published 2014 · Chemistry, Medicine

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Two mild and metal-free methods for the preparation of two kinds of important benzothiazole derivatives, 2-acylbenzothiazoles and dialkyl benzothiazol-2-ylphosphonates, respectively, were developed. The dialkyl H-phosphonate (RO)2P(O)H exists in equilibrium with its tautomer dialkyl phosphite (RO)2POH. TBHP triggered α-carbon-centered phosphite radical formation, whereas DTBP triggered phosphorus-centered phosphonate radical formation. The two types of radicals led respectively to two different reaction processes, the direct C2-acylation of benzothiazoles and C2-phosphonation of benzothiazoles.
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