Summary
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1.
Trimethylbromosilane and trimethylchlorosilane cleaved tetrahydrofuran, giving l-bromo-4-trimethylsilyloxybutane, and correspondingly, 1-chloro-4-trimethylsilyloxybutane.
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2.
Trimethylchlorosilane cleaves the tetrahydropyran ring, from which 1-chloro-5-trimethylsilyloxypentane and polymeric products are formed.
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3.
Two product, 1,5-dibromopentane and 1-bromo-5-trimethylsilyloxypentane, are obtained by cleaving tetrahydropyran with trimethylbromosilane.
Literature cited
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Zakharkin, L.I., Stanko, V.I. & Brattsev, V.A. Reaction of tetrahydrofuran and tetrahydropyran with trimethylbromosilane and trimethylchlorosilane. Russ Chem Bull 10, 1938–1940 (1961). https://doi.org/10.1007/BF01184741
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DOI: https://doi.org/10.1007/BF01184741