𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Mechanism of the pinacol–pinacolone rearrangement of 2,3-di-(3-pyridyl)-2,3-butanediol in sulfuric acid

✍ Scribed by Eric Loeser; Guang-Pei Chen; Tao He; Kapa Prasad; Oljan Repič

Book ID
104250667
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
180 KB
Volume
43
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

The reaction of 2,3-di-(3-pyridyl)-2,3-butanediol (1) in H 2 SO 4 was studied. It was found that the meso and racemic forms give mono-and bis-SO 3 addition products, which rearrange to a ketone (Metopirone ® ) and two other major by-products. The formation of SO 3 addition products and a marked increase in reaction rates with greater amount of SO 3 suggest an alternate mechanism involving sulfonyloxy leaving groups.

📜 SIMILAR VOLUMES

Pinacol-Pinacolone Rearrangement of 1, 2
Pinacol-Pinacolone Rearrangement of 1, 2-Di-(p-methoxyphenyl)-ethane-1, 2-diol and Bis-(4-methoxyphenyl)-acetaldehyde in Acid Media
✍ Wadie Tadros; Alfy Badie Sakla; Sami Bassili Awad; Abdul-Aziz Amine Helmy 📂 Article 📅 1972 🏛 John Wiley and Sons 🌐 German ⚖ 338 KB

## Abstract 1, 2‐Di‐(__p__‐methoxyphenyl)‐ethane‐1, 2‐diol gave in acid media bis‐(4‐methoxy‐phenyl)‐acetaldehyde, 4‐4′‐dimethoxy‐deoxybenzoin, and 1, 2‐di‐(__p__‐methoxyphenyl)‐ethylene oxide; their respective yields being influenced by at least 3 factors: (i) the acid, (ii) its concentration, and