On the Distribution of Oxygen-18 in Triphenylmethyl Benzoate from the Reaction of Triphenylmethyl and Benzoyl Peroxide carbonyl-<sup>18</sup>O

Doering, W. von E.; Okamoto, Kunio; Krauch, Helmut

doi:10.1021/ja01499a026

Cited by 16 publications

(1 citation statement)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The solvent radical would add to the benzoyl peroxide to form the benzoyloxyl radical and an ester (in diethyl ether, 1-ethoxyethyl benzoate was isolated in 95% yield) . Thermolysis of 18 O-labeled benzoyl peroxide, in which the carbonyl oxygen was labeled, and triphenylmethane in benzene produced triphenylmethyl benzoate as the major product in which most of the 18 O remained in the carbonyl group, indicating that the triphenylmethyl radical attacked the peroxidic oxygen atom . In the thermolysis of 8 , thermochemical estimates predict 20,21 the addition of the phenyl radical to the carbonyl oxygen is favored over radical addition to the ether oxygen as observed for benzoyl peroxide.…”

Section: Referencesmentioning

confidence: 99%

Pyrolysis of Aromatic Carboxylic Acids: Potential Involvement of Anhydrides in Retrograde Reactions in Low-Rank Coal

1997

View full text Add to dashboard Cite

The pyrolysis of 1-(3-carboxyphenyl)-2-(4-biphenyl)ethane (3) has been studied in the liquid phase at 400 °C neat and diluted in hydrogen-donor and nondonor solvents to determine the role of decarboxylation of aromatic carboxylic acids in the cross-linking processes in low-rank coal. Decarboxylation was the dominant reaction pathway in the pyrolysis of this model compound, and decarboxylation occurred primarily by an acid-promoted ionic mechanism that does not lead to cross-linking. However, pyrolysis in a nondonor solvent produced a small amount of products containing a new aryl−aryl bond between 3 and the solvent that represents the formation of a cross-link associated with the decarboxylation process. These cross-linked products were found to be formed by a free-radical pathway and could be decreased by the addition of H2O or tetralin to the pyrolysis medium. It is proposed that the cross-linked products arise from the formation and subsequent decomposition of anhydrides during the pyrolysis of the acid. Pyrolysis of di-3,3‘-(2-(4-biphenyl)ethyl)benzoic anhydride and 1-(3-carboxaldehydephenyl)-2-(4-biphenyl)ethane was investigated to support the proposed free-radical formation of the cross-linked products. These results suggest that cross-linking processes in low-rank coals may not be directly related to the decarboxylation process but may indirectly result from intermediates formed from reactions of the aromatic carboxylic acids.

show abstract

Section: Referencesmentioning

confidence: 99%

Pyrolysis of Aromatic Carboxylic Acids: Potential Involvement of Anhydrides in Retrograde Reactions in Low-Rank Coal

1997

View full text Add to dashboard Cite

show abstract

Syntheses and uses of isotopically labelled carboxylic acids

Zieliński

1969

Carboxylic Acids and Esters (1969)

View full text Add to dashboard Cite

Preparation and uses of isotopically labelled peroxides

Ōae¹,

Fujimori²

1983

PATAI'S Chemistry of Functional Groups

View full text Add to dashboard Cite

On the Distribution of Oxygen-18 in Triphenylmethyl Benzoate from the Reaction of Triphenylmethyl and Benzoyl Peroxide carbonyl-¹⁸O

Cited by 16 publications

References 0 publications

Pyrolysis of Aromatic Carboxylic Acids: Potential Involvement of Anhydrides in Retrograde Reactions in Low-Rank Coal

Pyrolysis of Aromatic Carboxylic Acids: Potential Involvement of Anhydrides in Retrograde Reactions in Low-Rank Coal

Syntheses and uses of isotopically labelled carboxylic acids

Preparation and uses of isotopically labelled peroxides

Contact Info

Product

Resources

About

On the Distribution of Oxygen-18 in Triphenylmethyl Benzoate from the Reaction of Triphenylmethyl and Benzoyl Peroxide carbonyl-18O

Cited by 16 publications

References 0 publications

Pyrolysis of Aromatic Carboxylic Acids: Potential Involvement of Anhydrides in Retrograde Reactions in Low-Rank Coal

Pyrolysis of Aromatic Carboxylic Acids: Potential Involvement of Anhydrides in Retrograde Reactions in Low-Rank Coal

Syntheses and uses of isotopically labelled carboxylic acids

Preparation and uses of isotopically labelled peroxides

Contact Info

Product

Resources

About

On the Distribution of Oxygen-18 in Triphenylmethyl Benzoate from the Reaction of Triphenylmethyl and Benzoyl Peroxide carbonyl-¹⁸O