Methyl orthobenzoate hydrolysis; the rate-determining step

Wenthe, Ann Marie; Cordes, E. H.

doi:10.1016/0040-4039(64)83127-0

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B Kinetics and Mechanism Of Ortho Ester Hydrolysis1

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1967

1975

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Cited by 6 publications

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“…OR + ROH + 0,(15) II 0 that the hydrotrioxide intermediate is structurally related to ortho esters and to tetrahedral intermediates believed to occur in hydrolysis and alcoholysis of carboxylic esters. In fact, Deslongchamps, et a/., have extended their observations on acetal ozonolysis to a theoretical analy-…”

mentioning

confidence: 99%

Mechanism and catalysis for hydrolysis of acetals, ketals, and ortho esters

Cordes¹,

Bull²

1974

Chem. Rev.

363

226

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mentioning

confidence: 99%

Mechanism and catalysis for hydrolysis of acetals, ketals, and ortho esters

Cordes¹,

Bull²

1974

Chem. Rev.

363

226

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“…There is no evidence for accumulation of these carbonium salts in aqueous solution, and in at least one instance rate of disappearance of ortho ester and rate of formation of carboxylate ester were shown to be the same (292,293).…”

Section: B Kinetics and Mechanism Of Ortho Ester Hydrolysismentioning

confidence: 95%

Reactions of Ortho Esters Which Result in Carbon-Oxygen and Carbon-Halogen Bond Formation

1970

Carboxylic Ortho Acid Derivatives - Preparation and Synthetic Applications

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In this chapter are considered reactions of trialkyl orthocarboxylates and tetraalkyl orthocarbonates which result in the formation of new carbonoxygen or carbon-halogen bonds. In most of these reactions the ortho ester (or an alkoxycarbonium ion derived from it) functions as an alkylating agent.Many of these reactions are useful synthetic tools. These include formation and hydrolysis of cyclic ortho ester derivatives of diols and triols (which serve to protect the hydroxyl groups of the polyols, and provide means for their mild monoacylation), alkylation of phenols, enols and acids (to form ethers and esters), and conversion of carbonyl compounds to acetals and ketals. Other reactions, such as the alkylation of halogens by ortho esters, are of only limited synthetic utility, while still others, such as the acidcatalyzed hydrolyses of ortho esters, are of interest primarily because of the light they shed on the mechanisms of reactions of ortho esters with nucleophilic reagents.

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Mechanism and Catalysis for the Hydrolysis of Acetals, Ketals, and Ortho Esters

Cordes¹

1967

Progress in Physical Organic Chemistry

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Methyl orthobenzoate hydrolysis; the rate-determining step

Cited by 6 publications

References 3 publications

Mechanism and catalysis for hydrolysis of acetals, ketals, and ortho esters

Mechanism and catalysis for hydrolysis of acetals, ketals, and ortho esters

Reactions of Ortho Esters Which Result in Carbon-Oxygen and Carbon-Halogen Bond Formation

Mechanism and Catalysis for the Hydrolysis of Acetals, Ketals, and Ortho Esters

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