A Novel Synthesis of (β-Organochalcogenyl)allyl Phenyl Sulfoxides via Regioselective Hydrochalcogenation Reaction of 1,2-Allenyl Sulfoxides

Zhimeng Wu; Ruwei Shen; Lianjun Ren; Xian Huang

doi:10.1055/s-2005-869958

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A Novel Synthesis of (β-Organochalcogenyl)allyl Phenyl Sulfoxides via Regioselective Hydrochalcogenation Reaction of 1,2-Allenyl Sulfoxides

Zhimeng Wu^a, Ruwei Shen^a, Lianjun Ren^a, Xian Huang*^a,b
^a Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou 310028, P. R. China
Fax: +86(571)88807077; e-Mail: huangx@mail.hz.zj.cn;
^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China

Abstract

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Abstract

(β-Organochalcogenyl)allyl phenyl sulfoxides 2 were prepared by treatment of allenyl sulfoxides 1 with sodium organyl chalcogenolates in good yields. The reaction was regioselective, giving exclusively one isomer in all cases. The applications of (β-phenyltelluro)allyl phenyl sulfoxide 2d and (β-organosulfanyl)allyl phenyl sulfoxide 2m in organic synthesis were also described.

Key words

allenyl sulfoxide - hydrochalcogenation - regioselectivity

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