2432-83-9Relevant academic research and scientific papers
Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade
Thiel, Verena,Brinkhoff, Thorsten,Dickschat, Jeroen S.,Wickel, Susanne,Grunenberg, Joerg,Wagner-Doebler, Irene,Simon, Meinhard,Schulz, Stefan
experimental part, p. 234 - 246 (2010/04/29)
Bacteria of the Roseobacter clade are abundant marine bacteria and are important contributors to the global sulfur cycle. The volatiles produced by two of its members, Phaeobacter gallaeciensis and Oceanibulbus indolifex, were analyzed to investigate whether the released compounds are derived from sulfur metabolism, and which biosynthetic pathways are involved in their formation. Both bacteria emitted different sulfides and thioesters, including new natural compounds such as 5-methyl phenylethanethioate (16) and butyl methanesulfonate (21). The S-methyl alkanoates were identified by comparison with standards that were synthesized from the respective methyl alkanoates by a new method using an easily prepared aluminium/sulfur reagent. Phaeobacter gallaeciensis is also able to produce tropone (37) in large amounts. Its biosynthesis was investigated by various feeding experiments, showing that 37 is formed via a deviation of the phenylacetate catabolism. The unstable tropone hydrate 42 was identified as an intermediate of the tropone biosynthesis that was also released together with tropolone (38). The Royal Society of Chemistry 2010.
The Preparation of (Methylthio)- and (Methylseleno)-tri(alkyl or aryl)phosphonium Salts and Their Reactions with Carboxylic Acids and Alcohols
Haynes, Richard K.,Indorato, Carlo
, p. 1183 - 1194 (2007/10/02)
A series of (methylthio)- and (methylseleno)-triphenylphosphonium salts and the analogous tributylphosphonium salts have been prepared by methylation of the corresponding tertiary phosphine sulfides and selenides.Details of their 1H, 13C and 31P n.m.r. spectra are given.Whereas the (methylthio)- and (methylseleno)-triphenylphosphonium salts undergo rapid decomposition in the presence of tertiary ammonium carboxylates or tertiary amines, the (methylthio)- and (methylseleno)-tributylphosphonium salts convert such carboxylates into methanethiol and methaneselenol estersin acceptable yields.A tris(dimethylamino)(methylthio)phosphonium salt, on the other hand, converts benzoate into methyl benzoate in quantitative yield.Inferior yields of (methylthio)- and (methylseleno)-alkanes are obtained from two primary alcohols and the tributylphosphonium salts.
