Dithio Esters Research Articles

ChemInform Abstract: SULFENYLATION OF DITHIO ESTER ANIONS

AbstractDie Anionen der Dithioester (I) reagieren mit den Alkanthiosulfonaten (II) unter Bildung der S‐sulfenierten Produkte (III).

Sulfenylation of dithio ester anions

AbstractThe anions derived from dithio esters 1 react with alkyl alkanethiosulfonates in 1,2‐dimethoxyethane to give the S‐sulfenylated products 3. Nucleophilic reagents like potassium tert‐butoxide, dithio ester anions or ‐ in some cases ‐ even (liquid) ammonia catalyse the rearrangement of 3 into the C‐sulfenylated compounds 4. The latter compounds can be isolated directly, if the dithio ester anions 2 are allowed to react with thiosulfonates in liquid ammonia or with thiocyanates in dimethoxyethane or liquid ammonia.

Dithiiranes and Thiosulfines as Reactive Intermediates

The intermediacy of the CSS ring and/or its isomer appears likely from new experiments: reaction of (1) with morpholine leads via the unstable α-chloroalkyldisulfanes and the dithio esters (4) to stable products. (2)/(3) has not yet been trapped (R1,R2CI; R1PhS, R2Tos).

Negative ions in organic mass spectrometry. II—Negative ion mass spectra of simple thio and dithio esters.

AbstractThe 70 eV negative ion mass spectra of some simple aromatic and aliphatic thio and dithio esters are discussed. A characteristic fragmentation process, a rearrangement analogous to the nitro‐nitrite conversion of aromatic nitro compounds, is observed for aromatic thio esters.

Simple stereoselective version of the dithio ester thio-Claisen rearrangement leading to E-trisubstituted olefinic bonds

Simple stereoselective version of the dithio ester thio-Claisen rearrangement leading to E-trisubstituted olefinic bonds

Cyanomethyldithiobenzoate as a new reagent for the sequential degradation of peptides

The synthesis and purification of cyanomethyldithiobenzoate is described. This active dithio ester can be used for degrading peptides, stepwise from their amino end, under mild conditions.

Stable carbonium ions. XCIII. Protonated thion esters and dithio esters and their cleavage in fluorosulfuric acid-antimony pentafluoride solution

Stable carbonium ions. XCIII. Protonated thion esters and dithio esters and their cleavage in fluorosulfuric acid-antimony pentafluoride solution

1H-NMR chemische Verschiebungen von Thiocarbonsäure-äthylestern

We follow the changes of the chemical shifts of both the methylen groups and of the methyl group in esters of the type R-CH2-COO-CH2-CH3, R-CH2-COS-CH2-CH3, R-CH2-CSO -CH2 -CH3, and R -CH2 -CSS -CH2 -CH3. In passing from the normal ester to the thiol, thion, and dithio ester the chemical shifts of the groups mentioned change by characteristic amounts independent from R for the investigated systems. Deviations from the increment system are discussed.

Antiradiation Compounds XI. Sulfur-Containing Derivatives of Nitriles and Aminonitriles

Attempts to obtain iminothio esters and dithio esters from α-aminoacetonitrile gave stable products only with the amino group acylated by the carbobenzoxy function. An iminothio ester derived from β-aminopropionitrile was found to be relatively stable as the dihydrochloride, however. Examples of both α- and β-cyanoalkylthio-sulfates were found to be stable as the sodium salts. Antiradiation testing of the β-amino iminothio ester dihydrochloride and the α-cyanothiosulfate showed no protective properties. Attempts to obtain iminothio esters and dithio esters from α-aminoacetonitrile gave stable products only with the amino group acylated by the carbobenzoxy function. An iminothio ester derived from β-aminopropionitrile was found to be relatively stable as the dihydrochloride, however. Examples of both α- and β-cyanoalkylthio-sulfates were found to be stable as the sodium salts. Antiradiation testing of the β-amino iminothio ester dihydrochloride and the α-cyanothiosulfate showed no protective properties.