Nucleophilic substitution of SN1-active halides using zinc salts: Preparation of thiolacetates

Structure–Odor Correlations in Homologous Series of Alkanethiols and Attempts To Predict Odor Thresholds by 3D-QSAR Studies

“…The odor thresholds of the alkane-2-thiols showed a similar dependency on the chain length as found for the alkane-1-thiols (Table 2). With a minimum at C 5 , odor thresholds significantly increased up to 41,000 for C 10 . As found for the alkane-1-thiols, also for the alkane-2-thiols a change in odor qualities to fatty, soapy odor notes was observed with increasing carbon number (Table 2), and most of these thiols have been reported in foods before.…”

“…Besides strong signals for the molecular ion, mass spectra of the 1-(methylthio)alkanes, for example, 1-(methylthio)hexane ( Figure 4B), revealed characteristic fragments resulting from methyl elimination (m/z 117) and an α-cleavage (m/z 61, C 2 H 5 S + ). The 1-(methylthio)-alkanes showed a minimum in their odor thresholds for 1-(methylthio)heptane (Table 8), but with increasing chain length threshold values increased to 490 ng/L air for C 10 . The compounds in this homologous series showed predominantly metallic, sweet, and garlic-like aroma qualities, except the longchain homologues (C 9 , C 10 ) exhibiting fatty odor qualities (Table 8).…”

S-Alkyl Chlorothioformates from Xanthates

“…28 Zinc xanthate was used for the preparation of 1e. [29][30][31] All xanthates were purified by vacuum distillation and checked by GC/MS before use. NMR spectroscopy was performed on a Varian VX-400 spectrometer, with TMS as an internal standard.…”

A facile and practical method for the preparation of thioacetates from alkyl halides and sodium thioacetate catalysed by PEG400

“…For example, they can be used in the synthesis of α, β-unsaturated esters and lactones under very mild conditions. 1 Metal enolates derived from thioesters have been employed in asymmetric carbon-carbon bond formation 2 and in the synthesis of macrocyclic natural products. 3 Furthermore, the thioesters can be either oxidized to sulfonic acids 4 or hydrolysed to monothiols.…”

“…The reaction of alkyl halides with zinc thiolacetate has also been reported as an alternative approach. 1 However, zinc thiolaceate is not readily available and a troublesome procedure has to be performed for its preparation before use. Other methods for thioester synthesis involve cobalt carbonylcatalysed carbonylation of mercaptans, 8 the cobalt chloridecatalysed coupling of thiols and anhydrides, 9 cleavage of S-S bond by Sm/CoCl 2 or Sm/CoCl 2 • 6H 2 O system 10 and the use of polymer-supported thiolacetate ion.…”