1,3-Migration of chloride and azide substituents within organosilicon cations,and anchimeric assistance by the azido group |
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Institution: | 1. Department of Gastroenterological and General Surgery, St. Luke''s International University Hospital, 9-1 Akashi-cho, Chuo-ku, Tokyo 104-8560, Japan;2. Division of Hepato-Biliary-Pancreatic and Transplant Surgery, Department of Surgery, Graduate School of Medicine, Kyoto University, Kyoto, Japan |
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Abstract: | Migration of the Cl substituent takes place when (Me3Si)2C(SiMe2Cl)(SiEt2I) or (Me3Si)2C(SiEt2Cl)(SiMe2I) reacts with AgBF4, the product in each being a mixture of (Me3Si)2C(SiEt2Cl)(SiMe2F) and (Me3Si)2C(SiEt2F)(SiMe2Cl), and analogous migration of N3 occurs in the corresponding reaction of (Me3Si)2C-(SiEt2N3)(SiMe2Br). Anchimeric assistance by the N3 group facilitates the solvolysis of (Me3Si)2C(SiMe2N3)(SiMe2Br). |
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