A 1,3,5-Dioxazine

Loev, Bernard; Snader, Kenneth M.; Kormendy, Minerva F.

doi:10.1021/jo01024a520

Cited by 6 publications

(7 citation statements)

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“…(29) For instance, the displacement of the chloride 21 with AcOK (CH3CN, 18-crown-6 ether) gave methyl 3,5-Q-diacetyl-2,6-dideoxyfyxo-d-L-hexofuranoside, a precursor of 2-deoxy-L-fucose: Durgnat, J.-M.; Warm, A.; Vogel, P., manuscript in preparation.…”

Section: Methodsmentioning

confidence: 99%

Naked sugars as synthetic intermediates. Total synthesis of L-daunosamine

Warm¹,

Vogel²

1986

J. Org. Chem.

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Section: Methodsmentioning

confidence: 99%

Naked sugars as synthetic intermediates. Total synthesis of L-daunosamine

Warm¹,

Vogel²

1986

J. Org. Chem.

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“…The reactions of benzhydrol with ethyl acetoacetate (12) and acetylacetone (14) gave the expected β-dicarbonyl compounds (17) and (19) as the final products, [11] and Meldrum's acid (11) gave 3,3-diphenylpropanoic acid (16), almost certainly formed by hydrolysis and decarboxylation of the dioxanedione initially formed by C-alkylation of the enol (this type of formolysis and decarboxylation has been reported for other β-diesters [12] ). Surprisingly, however, neither diethyl malonate, nor ethyl cyanoacetate, nor malononitrile gave any C-alkylation products (which we had expected by analogy with, for example, the reactions of these active methylene compounds in the Knoevenagel and Claisen-Schmidt condensations.…”

Section: Oh Phmentioning

confidence: 66%

Reactions of Active Methylene Compounds with Benzhydrol During Solvolysis in Formic Acid

Gullickson¹,

Lewis²

2003

Aust. J. Chem.

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Formic acid reacts with benzhydrol to give benzhydryl formate, which reacts with active methylene compounds in refluxing formic acid to give either C-alkylation or Ritter reaction products. The product formed is determined by the equilibrium enol content of the active methylene compound. These reaction conditions avoid the use of halogenated reaction solvents, and the pure products are isolated without recourse to chromatography.

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“…This product clearly arises from the Ritter reaction of the nitrile with the benzhydryl cation, with the product initially formed from ethyl cyanoacetate undergoing subsequent ester hydrolysis and decarboxylation. TLC and 1 H NMR monitoring revealed that to the extent observable at 400 MHz, all the benzhydrol (8) is completely converted to benzhydryl for-mate (9) within 20 minutes under these reaction conditions. This is consistent with benzhydryl formate, which undergoes subsequent slower solvolysis to the benzhydryl cation (10), being the actual substrate for the reaction (Scheme 2).…”

Section: Methodsmentioning

confidence: 90%

“…In all cases, a fair to good isolated yield of the Ritter reaction product was obtained after 24 hours or less under reflux; in no case was the strong acid catalyst typical of the Ritter reaction 9 used. It is also worth noting that the major reaction product in each of these reactions was isolated directly from the crude reaction mixture by crystallization; no chromatography was required.…”

Section: Methodsmentioning

confidence: 97%