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

Lenardão, Eder J.¹  Silva, Thiago B. da¹  Universidade Federal de Pelotas, Pelotas¹  Cella, Rodrigo¹  Perin, Gelson¹  Universidade Federal de Santa Maria, Santa Maria¹  Jacob, Raquel G.¹ 

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

DOI  :  10.1590/S0103-50532006000500031

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

A new and efficient method was developed to prepare a-phenylseleno-b-substituted styrenes by reaction of diethyl a-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)-a-phenyl-a-b-unsaturated aldehydes, respectively in good yields. The hydrolysis of the vinyl selenides in presence of TiCl4 allowed the corresponding a-aryl acetophenones.

【 授权许可】

Unknown