The Reaction of Aldehydes with Aldimines<sup>1</sup>

Patrick, Tracy M.

doi:10.1021/ja01132a008

Cited by 33 publications

(12 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The imine is converted to the heterocyclic in from 5 to 3Oy0 yield per pass (106). N-n-Butylidenebenzylamine when refluxed with butyraldehyde gives the aldol condensation product, N-2-ethylhexen-2-ylidenebenzylamine, in 42% yield and a cyclic material in 32% (206).…”

Section: A Reactions Involving Ring Formationmentioning

confidence: 99%

The Chemistry of Imines.

Layer¹

1963

Chem. Rev.

989

458

View full text Add to dashboard Cite

Section: A Reactions Involving Ring Formationmentioning

confidence: 99%

The Chemistry of Imines.

Layer¹

1963

Chem. Rev.

989

458

View full text Add to dashboard Cite

“…This fraction then slowly decomposed with the formation of both more and less mobile compounds. Oligomers are formed not only from the original aldehyde but SCHIFF base (111) can directly dimerize with another molecule of an aldehyde [2], and form the intermediary dimeric SCHIFF base (IV) which is hydrolyzed into a dimeric aldehyde (11).…”

Section: Hmentioning

confidence: 99%

Reaction of oxidized lipids with protein Part 14. Aldolization reactions of lower alkanals in presence of nonlipidic substances

Pokorný¹,

Janitz²,

Víden³

et al. 1987

Nahrung

View full text Add to dashboard Cite

Propanal, butanal, pentanal, and hexanal were stored mixed with cellulose, cellulose impregnated with amino acids, or with proteins at 60 "C and pH = 5.8. Alkanals were partially oxidized, partially aldolized.The corresponding dimers were identified by gas chromatography and mass spectrometry. The aldolizdtion was catalyzed by primary amine groups of amino acids and proteins. Various nonvolatile aldolization and STRECKER degradation products were formed. Aldolization products imparted fruity, sweet and light odour notes to the reaction mixture, accompanied by mushroom, cheese-like and stale notes.

show abstract

“…Amines and aldehydes react rapidly to form a variety of products (Tschitschibabin, 1906;Patrick, 1952;Charman and Rowe, 1971; Kallen and Jencks, 1966;Hardy et al, 1976a,b). The pK,s of the amine-aldehyde adducts ( Fig.…”

Section: A Acid-base Eouil/bria Amines Amine D€rmentioning

confidence: 99%

Aldehyde fixatives: Quantification of acid‐producing reactions

Johnson

1985

J. Elec. Microsc. Tech.

View full text Add to dashboard Cite

Under conditions commonly used for the preservation of tissue for electron microscopy, substantial amounts of hydrogen ions were produced when either formaldehyde or glutaraldehyde was added to solutions of amines or proteins, or to tissue homogenates. In glycine-aldehyde reactions, hydrogen ions were generated in linear proportion to the glycine concentration over the range of 0.001 M to 0.100 M glycine. In the presence of 1% formaldehyde or 1% glutaraldehyde, 0.3-0.9 equivalents of acid were produced per mole of primary amine. This variation is a function of the specific primary amine used. Acid production increased with increasing formaldehyde concentration but did not iiicrease appreciably with increasing glutaraldehyde concentration. The concentration of amines in tissue is high. These amines are probably responsible for much of the acid generated when aldehydes react with tissue homogenates.In amine-aldehyde reactions, the positive charge originally associated with the parent amine is simultaneously neutralized with the formation of hydrogen ions. Thus, in tissues exposed to aldehydes, there is a decrease in the overall positive charge which is related to the amount of acid generated. The inherent buffering capacity of liver and muscle was not sufficient to prevent large pH decreases when aldehydes were added to homogenates of these tissues. These data suggest that significant but transient pH decreases may occur within cells exposed to aldehydes. To minimize the aldehyde-induced pH decreases, a buf'fer should be chosen so that its pK, is 0.2-0.3 pH units less than the pH desired for a particular experiment. In addition, buffer concentrations of at least 0.10 M are suggested for fixatives in order to provide adequate buffering capacity during tissue preservation.

show abstract

The Reaction of Aldehydes with Aldimines¹

Cited by 33 publications

References 0 publications

The Chemistry of Imines.

The Chemistry of Imines.

Reaction of oxidized lipids with protein Part 14. Aldolization reactions of lower alkanals in presence of nonlipidic substances

Aldehyde fixatives: Quantification of acid‐producing reactions

Contact Info

Product

Resources

About

The Reaction of Aldehydes with Aldimines1

Cited by 33 publications

References 0 publications

The Chemistry of Imines.

The Chemistry of Imines.

Reaction of oxidized lipids with protein Part 14. Aldolization reactions of lower alkanals in presence of nonlipidic substances

Aldehyde fixatives: Quantification of acid‐producing reactions

Contact Info

Product

Resources

About

The Reaction of Aldehydes with Aldimines¹