Investigation of the base promoted tandem syn-elimination–Favorskii rearrangement of levoglucosan sulfonates

Muldgaard, Lene; Thomsen, Ingrid K.; Hazell, Rita G.; Bols, Mikael

doi:10.1039/b200064b

Cited by 8 publications

(2 citation statements)

References 15 publications

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“…When the 2,3,4-tri-O-sulfonyl--D-glucopyranoses 139 (Scheme 48) were treated with sodium methoxide in a mixture of methanol and chloroform, the rearranged products 143 were obtained [64]. The proposed reaction mechanism involves elimination of the corresponding sulfonic acids followed by base-catalysed transesterification of the enol sulfonates formed, to give ketones 140 or 141, which on further reaction with sodium methoxide generate cyclopropanone 142.…”

Section: -Sulfonyloxy Ketonesmentioning

confidence: 99%

The Favorskii Rearrangement: Synthetic Applications

Guijarro¹,

Yus²

2005

COC

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Section: -Sulfonyloxy Ketonesmentioning

confidence: 99%

The Favorskii Rearrangement: Synthetic Applications

Guijarro¹,

Yus²

2005

COC

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“…Obviously, the chlorine atom in α-chloro ketone molecule II is not replaced directly by amino group, but the reaction involves Favorskii rearrangement [2]. The structure of amides III-IX was proved by their IR and 1 H and 13 C NMR spectra and elemental analyses, and their purity was checked by TLC.…”

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confidence: 99%

Reaction of 3-chloro-1-(2,4,6-trimethylphenyl)propan-2-one with amines

et al. 2009

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SHORT COMMUNICATIONSWhile continuing our studies in the fields of synthesis and transformations of 1,2-chlorohydrins [1] obtained by reaction of arenes with 3-chloro-1,2-epoxypropane in the presence of aluminum chloride, we performed oxidation of 3-chloro-1-(2,4,6-trimethylphenyl)propan-2-ol (I) with chromium(VI) oxide and isolated 3-chloro-1-(2,4,6-trimethylphenyl)propan-2one (II). α-Chloro ketone II was brought into reaction with various primary amines in aqueous potassium hydroxide at room temperature. The reaction time was 20-45 min. Regardless of the amine nature, in all cases the products were the corresponding N-substituted 3-(2,4,6-trimethylphenyl)propionamides III-IX which were isolated in 50-97% yield as colorless crystalline substances and were recrystallized from ethanol.

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Favorskii Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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The Favorskii rearrangement is a base‐induced rearrangement of α‐halo ketones to the corresponding carboxylic acid derivatives (e.g., acids, esters, and amides) with the same number of carbon atoms in the skeletons; and the bases can be hydroxide, alkoxide, or amines. There have been at least six different mechanisms presented for this rearrangement. Among these mechanisms, the semibenzilic acid mechanism and cyclopropanone mechanisms are most plausible. Besides this, many experimental results have shown that the actual reaction mechanisms depend on the reaction conditions. This reaction has wide application for the synthesis of highly strained esters, bicyclic esters, some steroids, etc.

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Investigation of the base promoted tandem syn-elimination–Favorskii rearrangement of levoglucosan sulfonates

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 8 publications

References 15 publications

The Favorskii Rearrangement: Synthetic Applications

The Favorskii Rearrangement: Synthetic Applications

Reaction of 3-chloro-1-(2,4,6-trimethylphenyl)propan-2-one with amines

Favorskii Rearrangement

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