Structure and properties of sulfur-containing compounds. IV. Study of the reactivity of sulfur atom in 3-substituted thianaphthenes in oxidation with perbenzoic acid

1969 ◽  
Vol 34 (8) ◽  
pp. 2417-2428 ◽  
Author(s):  
N. Kucharczyk ◽  
V. Horák
Author(s):  
Yamato Miyazawa ◽  
Kenji Kawaguchi ◽  
Ryo Katsuta ◽  
Tomoo Nukada ◽  
Ken Ishigami

ABSTRACT DAMASCENOLIDETM [1, 4-(4-methylpent-3-en-1-yl)furan-2(5H)-one], which is isolated from damask rose, is a useful aroma compound with a citrus-like odor. We have previously reported on the synthesis and odor properties of 34 analogs of 1 as part of our new aroma compound development project. In order to develop better aroma compounds and to gather more information on structure-odor relationships, six novel sulfur-containing analogs of 1 were synthesized. Odor evaluation revealed that their odors differed significantly from those of the corresponding sulfur-free compounds. The introduction of a sulfur atom does not necessarily result in a sulfur-like odor. In particular, the 2(5H)-thiophenone analogs gave waxy, oily and lactone-like odors that are uncharacteristic of sulfur-containing compounds. In many synthesized analogs, the introduction of a sulfur atom led to an increase in odor intensity, as expected.


1986 ◽  
Vol 64 (8) ◽  
pp. 1620-1629 ◽  
Author(s):  
Lucjan J.J. Hronowski ◽  
Walter A. Szarek

Three new carbocyclic analogs of nucleosides having the 2-thiouracil base have been synthesized. The cyclopentyl groups in these nucleosides are (±)-{(1β,3α,4β)-3-hydroxy-4-(hydroxyrnethyl)cyclopentyl} (see 31), (±)-{(1β,2α,4β)-2-hydroxy-4-(hydroxymethyl)cyclopentyl} (see 32), and (±)-{(1β,2α,3α,4β)-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl} (see 33). The nucleosides were prepared by coupling the appropriate hydroxy derivatives of cis-3-aminocyclopentanemethanol with 3-ethoxypropenoyl isothiocyanate (21) followed by cyclization in 15 N aqueous ammonia to give the 2-thiouracil nucleosides. In addition a modified and shortened synthetic route is described for the synthesis of (±)-(1β,2α,3α,4β)-4-amino-2,3-dihydroxy-cyclopentanemethanol (19). The 1H nmr spectra at 200 MHz of all of the synthetic intermediates, the 2-thiouracil nucleosides, and of the corresponding carbocyclic analogs of uracil nucleosides are discussed. It is shown that each nucleoside has a characteristically unique 1H nmr spectrum and that in general the protons in the sulfur-containing compounds resonate at lower fields than those in the corresponding oxygen-containing compounds. The magnitude of this downfield shift is inversely related to the number of bonds separating a particular proton from the sulfur atom.


Author(s):  
Aleksandar Bojkovic ◽  
Thomas Dijkmans ◽  
Hang Dao Thi ◽  
Marko Djokic ◽  
Kevin M. Van Geem

2019 ◽  
Vol 17 (2) ◽  
pp. 499-508 ◽  
Author(s):  
Galina S. Pevneva ◽  
Natalya G. Voronetskaya ◽  
Nikita N. Sviridenko ◽  
Anatoly K. Golovko

AbstractThe paper presents the results of investigation of changes in the composition of hydrocarbons and sulfur-containing compounds of an atmospheric residue in the course of cracking in the presence of a tungsten carbide–nickel–chromium (WC/Ni–Cr) catalytic additive and without it. The cracking is carried out in an autoclave at 500 °C for 30 min. The addition of the WC/Ni–Cr additive promotes the deepening of reactions of destruction not only of resins and asphaltenes, but also high molecular weight naphthene-aromatic compounds of the atmospheric residue. It is shown that the content of low molecular weight C9–C17 n-alkanes and C9–C10 alkylbenzenes rose sharply in the products of cracking with addition of WC/Ni–Cr in comparison with those produced without the additive. Alkyl- and naphthene-substituted aromatic hydrocarbons of benzene, naphthalene, phenanthrene series, polyarenes, benzo- and dibenzothiophenes are identified.


1980 ◽  
Vol 11 (3) ◽  
pp. 208-210
Author(s):  
E. P. Ovchinnikova ◽  
L. S. Abramova ◽  
Z. A. Rogovin

Sign in / Sign up

Export Citation Format

Share Document