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Trifluoromethanesulfonic Acid Catalyzed Alkylation of Arenes with Methyl (2R)-Glycidate

✍ Scribed by Pablo J. Linares-Palomino; G. K. Surya Prakash; George A. Olah

Book ID
102260187
Publisher
John Wiley and Sons
Year
2005
Tongue
German
Weight
173 KB
Volume
88
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Methyl (R)‐glycidate (=methyl (R)‐oxiranecarboxylate; 2) in superacidic trifluoromethanesulfonic acid medium reacts with electron‐rich arenes to give α‐hydroxy‐β‐arylpropanoate derivatives 3a–3f with high stereospecificity. At the same time, the observed high regioselectivity has been attributed to superelectrophilic activation of the glycidate.

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Acidity dependence of the trifluorometha
Acidity dependence of the trifluoromethanesulfonic acid catalyzed isobutane-isobutylene alkylation modified with trifluoroacetic acid or water
✍ George A. Olah; Patrice Batamack; Denis Deffieux; Béla Török; Qi Wang; Árpád Mol 📂 Article 📅 1996 🏛 Elsevier Science 🌐 English ⚖ 516 KB

Trifluoromethanesulfonic acid (TFSA) catalyzed isobutane-isobutylene alkylation modified with trifluoroacetic acid (TFA) or water, was studied over a wide range of acidity (Ho: -10.1 to -14.1). The effect of the acidity of these nonoxidizing strong mixed acid systems on the alkylation, is reported.