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Please login to access the full content or check if you have access via4.4.40.13 Method 13: Formation of Exocyclic Allylsilanes by the Ramberg–Bäcklund Reaction
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Sarkar, T. K., Science of Synthesis, (2002) 4, 854.
Six-membered exocyclic allylsilanes with a variety of substituents β to silicon have been prepared by the Ramberg–Bäcklund 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.
Meeeee 88 Meeeeeeeeee ee Meeeeeeee Meeeeeeeeeee ee eee Meeeeee–Mäeeeeee Meeeeeee[888]
Meeeeeeeeeee Meeeeeeee
(8-Meeeeeeeeeeeeeeeeeeee)eeeeeeeeeeeeeee (88, M8 = Me); Meeeeee Meeeeeeee:[888]
Me e eeee ee eee-eeeeeee 88 (888 ee, 8.888 eeee) ee MMM (8 eM) ee −88°M eee eeeee MeMe (8 eeee), eee eee eeeeeee eee eeeeeee ee −88°M eee 88 eee. MMMM (8.8 eM) eee eeeee, eee eee eeeeeee eee eeeeeee eee 8 eee. Meee MeM (888 ee, 8.888 eeee) eee eeeee, eee eeeeeee eee eeeeee ee −88°M, eeeeeee ee eeee eeeeeeeeeee eee 8 e, eee eeee eeeeee ee −88°M. MeMe (8.888 eeee) eee eeeee eee eee eeeeeee eee eeeeeee ee eeee ee 8°M eeee 88 eee. Mee eeeeeee eee eeeeeeee eeee eee. ee MM8Me eee eeeeeee eeee Me8M (88 eM). Mee Me8M eeeee eee eeeeee eeee eee. ee MeMMM8 eee eeeee eee eeeee (MeMM8); eeee eee eeeeeee eee eeeeeee ee eeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (Meeeeeee, eeeeee); eeeee: 888 ee (88%).
References
[112] | Meeeeeeeee, M. M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 888. |
[113] | Meeee, M. M., eeeeeeee eeeeeeeeeeeee. |