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首页> 外文期刊>Bulletin of the Chemical Society of Japan >'Syn-Effect' in the Isomerization of (E)-alpha-Fluorovinylic Sulfones to the Corresponding Allylic Sulfones under Basic Conditions
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'Syn-Effect' in the Isomerization of (E)-alpha-Fluorovinylic Sulfones to the Corresponding Allylic Sulfones under Basic Conditions

机译：在碱性条件下（E）-α-氟代丙烯腈砜异构化为相应的烯丙基砜中的“同步效应”

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摘要

Toward the elucidation of the origin of the “syn-effect,” the stereochemistry of the isomerization of (E)-alpha-fluorovinylic sulfones to the corresponding allylic sulfones under mild basic conditions was investigated. The ratio of (Z)-iso-mers of the resulting allylic sulfones decreased in the following order for the gamma-substituents of the starting vinylic sulfones: F->EtO->CH_3->BnS->CH_3CH_2-(CH_3)_2>(CH_3)_3-, C_6H_5-. The fluorine atom showed the highest “syn-effect,” which is herein defined as an effect that stabilizes the syn-conformation in the transition state against a steric or nonbonded repulsion; the rest of the series was in accord with previus results found in the conversion of alpha-unsubsti-tuted (E)-vinylic sulfones to the corresponding allylic sulfones under similar conditions. Theses results were rationalized based on the sigma->pi interaction.
机译：为了阐明“同步效应”的起源，研究了在温和的碱性条件下将（E）-α-氟乙烯砜异构化为相应的烯丙基砜的立体化学。对于起始乙烯基砜的γ-取代基，所得烯丙基砜的（Z）-异构体比例按以下顺序降低：F-> EtO-> CH_3-> BnS-> CH_3CH_2-（CH_3）_2> （CH_3）_3-，C_6H_5-。氟原子显示出最高的“合成效应”，在本文中定义为稳定过渡态中的合成构象抵抗空间或非键排斥的效应。该系列的其余部分与在类似条件下将未经取代的α-乙烯基取代的（E）-乙烯基砜转化为相应的烯丙基砜的结果相符。这些结果基于sigma-> pi相互作用进行了合理化。

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