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Further evidence to understand the stereochemistry of the reactions of α-sulfinyl carbanions

✍ Scribed by Atsuyoshi Ohno; Masato Higaki; Mutsuo Okamura

Book ID
102846539
Publisher
John Wiley and Sons
Year
1992
Tongue
English
Weight
541 KB
Volume
3
Category
Article
ISSN
1042-7163

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✦ Synopsis

0 BuLi/THFIA,C=O} hHR c [ OD/020,CDaOD BuLilTHF/D20 BuLi/THF/Mei -Hs

The stereochemistry of the a-sulfinyl carbanion has been studied. It has been elucidated that a 2-pyridylmethyl substituent on the sulfinyl sulfur chelates onto the counter cation in an ion pair to fix the conformation of the anion at a particular orientation. Then, the steric bulk of the other substituent plays a role to control the reacting face. A soft electrophile such as methyl iodide attacks the anion from the more open side. On the other hand, a hard electrophile such as a proton is initially trapped by the polar part of the ion pair and no steric effect operates.

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Stereochemistry in the reaction of alkyl
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✍ Masato Higaki; Mutsuo Goto; Atsuyoshi Ohno 📂 Article 📅 1990 🏛 John Wiley and Sons 🌐 English ⚖ 413 KB

Stereochemistry of the reactions of methyl-, ethyl-, 2propyl-, and 1 ,I -dimethylethylsulfinyl phenylmethyl carbanions with deuterium oxide and methyl iodide in tetrahydro furan have been studied. The 2-propylsulfinyl phenylmethyl carbanion exerts abnormal behavior in the sense that the alkyl substi