Synthesis and reactivity of alpha-phenylseleno-beta-substituted styrenes: preparation of (Z)-allyl alcohols, (E)-alpha-phenyl-alpha,beta-unsaturated aldehydes and alpha-aryl acetophenones

Journal of the Brazilian Chemical Society

Eder J. Lenardão²  Rodrigo Cella¹  Raquel G. Jacob²  Thiago B. Da Silva²  Gelson Perin¹ 

[1] ,Universidade Federal de Pelotas Departamento de Química Analítica e Inorgânica Pelotas RS

关键词: Horner-Wittig reactions;    vinyl selenides;    transmetallation;    a-b-unsaturated aldehydes;    Z-allyl alcohols;   

DOI  :  10.1590/S0103-50532006000500031

来源: SciELO

【 摘 要 】

A new and efficient method was developed to prepare alpha-phenylseleno-beta-substituted styrenes by reaction of diethyl alpha-phenylseleno benzylphosphonate with NaH and aldehydes. Selenium-lithium exchange by reaction with n-BuLi yielded the vinyl lithium species, which were captured with several electrophiles, like aldehydes and DMF, affording exclusively (Z)-allyl alcohols, and (E)-alpha-phenyl-alpha-beta-unsaturated aldehydes, respectively in good yields. The hydrolysis of the vinyl selenides in presence of TiCl4 allowed the corresponding alpha-aryl acetophenones.

【 授权许可】

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