1,3-Dioxolan-2-ylium and related heterocyclic cations

Pittman, Charles U.; McManus, Samuel P.; Larsen, John W.

doi:10.1021/cr60278a003

Cited by 134 publications

(48 citation statements)

References 65 publications

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“…The combined ethereal extracts were washed with water and dried with MgSO,. After the ethereal extracts were dry, the solution was concentrated by rotary evaporator and the vacuum distilled with a short fractionating column; bp 74-76OCI0.5 Torr (1 …”

Section: Preparation Of Etl~yl-2-etl~oxymethyl Malonatementioning

confidence: 99%

“…The acid-catalysed reactions of carboxylic acids, carboxylic acid derivatives, and orthoesters involve the transient formation of carbenium ions with two oxygen-containing substituents (1). These substituents can be either hydroxy, alkoxy, aryloxy, or combinations of these groupings depending on the nature of the reaction under consideration.…”

Section: Introductionmentioning

confidence: 99%

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Structural studies on dioxan-2-ylium ions; intramolecular attack of an oxygen atom on a carbenium ion centre

Childs¹,

Kang²,

Wark³

et al. 1994

Can. J. Chem.

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). As models for the ionization of orthoesters, a series of 1,3-dioxan-2-ylium salts have been prepared and characterized. The properties of 1,3-dioxan-2-ylium hexachloroantimonate 1, 5-ethoxymethyl-1,3-dioxan-2-ylium hexachloroantimonate 2, 2-methyl-5-ethoxymethy 1-1,3-dioxan-2-ylium hexachloroantimonate 3, and 2-phenyl-5-ethoxymethyl-1,3-dioxan-2-ylium hexachloroantimonate 4, have been studied by 'H and I3C NMR spectroscopy. The structures of 3 and 4 have been determined using X-ray crystallography. Salts 3 and 4 both crystallize in monoclinic crystal systems. For 3, the space group is C2/c, with a est dispose au-dessus du cycle dioxan-2-ylium. Toutefois, l'interaction entre l'oxygbne de 1'Cther et le centre cationique n'est pas important du B la grande distance internuclkaire qui est observCe. On a prepare le cation 5 dans lequel la longueur de la chaine carbonCe entre l'oxygbne de 1'Cther et le C(5) est augmentCe. On a trouvC que cet ion subit un rearrangement intramoleculaire rCversible conduisant B la formation de 1'hexachloroantimonate du 1-mCthyl-4-acCtoxymCthyl-tCtrahydrofurany1 oxonium.[Traduit par la rkdaction]

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Section: Preparation Of Etl~yl-2-etl~oxymethyl Malonatementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structural studies on dioxan-2-ylium ions; intramolecular attack of an oxygen atom on a carbenium ion centre

Childs¹,

Kang²,

Wark³

et al. 1994

Can. J. Chem.

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“…Similarly, various N-allylamides and related compounds give products of oxygen (sulfur) rather than nitrogen participation (5,16,17). Table 1, however, none was considered to be of therapeutic value.…”

Section: Resultsmentioning

confidence: 99%

Synthetic morphinans and hasubanans. VI. Total synthesis of 3-hydroxyisomorphinans, 3-hydroxyhasubanans, and 3,9-dihydroxyhasubanans

Monković¹,

Wong²

1976

Can. J. Chem.

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Ivo Mo~~ovrd and HENRY WONG. Can. J. Chem. 54,883 (1976).A new total synthesis of racemic 3-hydroxyisomorphinans (3), 3-hydroxyhasubanans (9), 3,9a-dihydroxyhasubanans (5), and 3,9p-dihydroxyhasubanans (7), via 4a-(2-aminoethy1)-1,2,3,4,4a,9-hexahydro-6-methoxyphenanthrene ( l a ) is described.Ivo MONKOVI~ et HENRY WONG. Can. J. Chem. 54, 883 (1976).On dkrit une nouvelle synthbse totale des hydroxy-3 isomorphinanes (3), hydroxy-3 hasubananes (9), dihydroxy-3,9a hasubananes (5) et dihydroxy-3,9p hasubananes (7) par I'intermCdiaire du (amino-2 Cthy1e)-4a hexahydro-1,2,3,4,4a,9 mCthoxy-6 phknanthrkne (la).

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“…The iminium ether intermediate ii has ambident electrophilicity, and the C2 and C4 positions of the oxazoline ring can react with nucleophiles. [22][23][24][25][26][27][28][30][31][32][33] Methyl ether 3a′ is not produced, and therefore nucleophilic attack by MeOH on intermediate ii selectively occurs at the C2 position rather than the C4 position of the oxazoline ring, to give a possible intermediate iii, which affords alcohol 3a on aqueous work-up.…”

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confidence: 99%

Oxidative Rearrangement of Cyclobutanone Derived <i>N</i>,<i>O</i>-Ketals Leading to Pyrrolidone Derivatives

et al. 2015

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1,3-Dioxolan-2-ylium and related heterocyclic cations

Cited by 134 publications

References 65 publications

Structural studies on dioxan-2-ylium ions; intramolecular attack of an oxygen atom on a carbenium ion centre

Structural studies on dioxan-2-ylium ions; intramolecular attack of an oxygen atom on a carbenium ion centre

Synthetic morphinans and hasubanans. VI. Total synthesis of 3-hydroxyisomorphinans, 3-hydroxyhasubanans, and 3,9-dihydroxyhasubanans

Oxidative Rearrangement of Cyclobutanone Derived <i>N</i>,<i>O</i>-Ketals Leading to Pyrrolidone Derivatives

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