Control of regio- and stereoselectivity in electrophilic addition reactions of allenes

Ma, Shengming

doi:10.1351/pac200779020261

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Pure Appl. Chem., 2007, Vol. 79, No. 2, pp. 261-267

http://dx.doi.org/10.1351/pac200779020261

Control of regio- and stereoselectivity in electrophilic addition reactions of allenes

Shengming Ma

Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027 and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China

Abstract: The halohydroxylation reaction of 1,2-allenyl sulfoxides exhibits E-selectivity while those of analogous sulfides and selenides show Z-selectivity. Rationales for the stereoselectivities are proposed. The reaction of 2,3-allenols with X⁺ affords 3-halo-2,5-dihydrofurans or 3-halo-3-enals depending on the nature of the alcohols.