Title of article
Mechanism of the pinacol–pinacolone rearrangement of 2,3-di-(3-pyridyl)-2,3-butanediol in sulfuric acid
Author/Authors
Loeser، نويسنده , , Eric Y.H. Chen، نويسنده , , Guang-Pei and He، نويسنده , , Tao and Prasad، نويسنده , , Kapa and Repic، نويسنده , , Oljan and Blacklock، نويسنده ,
Issue Information
هفته نامه با شماره پیاپی سال 2002
Pages
5
From page
2161
To page
2165
Abstract
The reaction of 2,3-di-(3-pyridyl)-2,3-butanediol (1) in H2SO4 was studied. It was found that the meso and racemic forms give mono- and bis-SO3 addition products, which rearrange to a ketone (Metopirone®) and two other major by-products. The formation of SO3 addition products and a marked increase in reaction rates with greater amount of SO3 suggest an alternate mechanism involving sulfonyloxy leaving groups.
Keywords
methyl migration , Pinacol–pinacolone rearrangement , pyridinyl migration
Journal title
Tetrahedron Letters
Serial Year
2002
Journal title
Tetrahedron Letters
Record number
1650598
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