77411-96-2Relevant academic research and scientific papers
One-pot dialkylation of allylphenylsulfide induced by aminoalkoxides- activated NaNH2. Application to the synthesis of unsymmetrical ketones
Choppin, Sabine,Gros, Philippe,Fort, Yves
, p. 9261 - 9268 (2007/10/03)
It is shown that the activation of NaNH2 by sodium aminoalkoxides, leading to new superbases, induced an efficient one-pot dialkylation of allylphenylsulfide. The regioselectivity of the reaction (α,α' vs α,γ) was found as strongly dependent on the nature of the alkyl halide. As an application, α,γ dialkylated products were efficiently converted Into the corresponding unsymmetrical ketones.
The Formation of Allyl Sulphides by Phenylthio-migration: Control by Silicon
Fleming, Ian,Paterson, Ian,Pearce, Andrew
, p. 256 - 262 (2007/10/02)
When γ-silyl-β-phenylthio-alcohols are treated with acid, the strategically placed silyl group encourages the rearrangement of the phenylthio-group, both from a secondary migration origin to a secondary migration terminus, and from a secondary migration origin to a tertiary migration terminus (4)->(6).Geraniol/nerol (12) and linalool (14) have been synthesised from a common intermediate (11) using this type of reaction.Phenylthio-migration from a tertiary migration origin (17)->(3) can be controlled to a limited extent by a suitably placed silyl group, but it is easier to achieve direct β-elimination of the silyl and phenylthio-groups (17)->(18).
