Studies on electrophilic reaction of Br2 with 1,2-allenylic sulfones. A highly regio- and stereoselective synthesis of 1-phenylsulfonyl-2-bromo-1(E)-alken-3-ols and 1-phenylsulfonyl-2-bromo-1(E),3(E)-butadienes |
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| Authors: | Chao Zhou Shengming Ma |
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| Institution: | a Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, PR China
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, PR China |
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| Abstract: | The reaction of 1,2-allenyl sulfones with Br2 afforded E-bromohydroxylation- or E-bromination-elimination products highly regio- and stereoselectively depending on the substitution pattern of the allene functionality. The five-membered intermediate cis-3h was isolated and characterized by X-ray diffraction study. The study on its reactivity of this intermediate revealed the origin of the regio- and stereoselectivity of this reaction. |
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| Keywords: | 1 2-Allenylic sulfones Bromine Bromohydroxylation Mechanistic study |
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