1381982-63-3Relevant academic research and scientific papers
Lewis Acid Catalyzed Transfer Hydromethallylation for the Construction of Quaternary Carbon Centers
Walker, Johannes C. L.,Oestreich, Martin
, p. 15386 - 15389 (2019)
The design and gram-scale synthesis of a cyclohexa-1,4-diene-based surrogate of isobutene gas is reported. Using the highly electron-deficient Lewis acid B(C6F5)3, application of this surrogate in the hydromethallylation of electron-rich styrene derivatives provided sterically congested quaternary carbon centers. The reaction proceeds by C(sp3)?C(sp3) bond formation at a tertiary carbenium ion that is generated by alkene protonation. The possibility of two concurrent mechanisms is proposed on the basis of mechanistic experiments using a deuterated surrogate.
Carbon-based leaving group in substitution reactions: Functionalization of sp3-hybridized quaternary and tertiary benzylic carbon centers
Mahoney, Stuart J.,Lou, Tiantong,Bondarenko, Ganna,Fillion, Eric
, p. 3474 - 3477 (2012/09/05)
Lewis acid promoted substitution reactions employing Meldrum's acid and 5-methyl Meldrum's acid as carbon-based leaving groups are described which transform unstrained quaternary and tertiary benzylic Csp 3-Csp3 bonds into Csp3-X bonds (X = C, H, N). Importantly, this reaction has a broad scope in terms of both suitable substrates and nucleophiles with good to excellent yields obtained (typically >90%).
