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Please login to access the full content or check if you have access via Method 13: Formation of Exocyclic Allylsilanes by the Ramberg–Bäcklund Reaction

DOI: 10.1055/sos-SD-004-00909

Sarkar, T. K.Science of Synthesis, (20024854.

Six-membered exocyclic allylsilanes with a variety of substituents β to silicon have been prepared by the RambergBäcklund alkenation reaction of α-sulfonyl sulfones.[‌112‌] For example, treatment of bis-sulfone 57 with butyllithium at 78°C, followed by warming to room temperature, yields allylsilane 58 (R1=H) (Scheme 26).[‌112‌] If the lithiated sulfone from 57 is alkylated, and a second equivalent of butyllithium is added, β-substituted allylsilanes, for example, 58 (R1=Me, Bn), may be synthesized by this protocol. Bis-sulfone 57 is available from cyclohexyl phenyl sulfone (56) by lithiation followed by sulfenylation and oxidation with 3-chloroperoxybenzoic acid.

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