16000-67-2

Upstream product

• 16000-64-9 meso-tetradeca-5,9-diyne-7,8-diol 
• 131543-46-9 Glyoxal 
• 3761-92-0 n-hexylmagnesium bromide 
• 1846-67-9 hept-2-ynal 
• 18232-30-9 1,1-diethoxy-2-heptyne 
• 16000-63-8 racem.-tetradeca-5,9-diyne-7,8-diol 
• 41446-63-3 (E)-7-tetradecene 
• 111-71-7 heptanal 
• 32359-01-6 hexenylmagnesium bromide 
• 693-02-7 hex-1-yne 

Relevant academic research and scientific papers

Facile pinacol coupling of aliphatic ketones by Brook rearrangement in the presence of samarium species

Herein we report a practical pinacol coupling reaction, in which ketones (aldehydes) react smoothly with Sm and TMSBr to afford the diol products with Sm(II) or (III) siliyl species generated in situ. This reported method affords poor yields for aromatic ketone substrates and good yields for aliphatic ketones. Therefore, it distinguishes from most reductive coupling approaches that are more effective for aromatic carbonyl compounds and provides a facile and robust approach for the pinacol coupling of aliphatic ketones. Mechanistic studies also indicated the pinacolization probably proceeded via an anionic instead of radical coupling pathway involving the Brook rearrangement in the presence of samarium (II or III) silyl species.

Ruthenium Tetroxide Oxidation of Alkenes. A More Complete Picture

The ruthenium tetroxide oxidation of some linear and cyclic alkenes, representatives of five substitution patterns, has been performed in acetone-water (5:1) solution at -70 deg C using stoichiometric ammounts of the oxidant.The main reaction products are 1,2-diols and/or α-ketols depending on the nature of the substrate little amounts of scission products, aldehydes and/or carboxylic acids, are also obtained.Generally 1,2-diols predominate over α-ketols except in the oxidation of (-)-α-pinene that afforded the α-ketol in 51percent yield while no trace of the corresponding 1,2-diol was detected.All reactions prceeded through the formation of unstable brownish precipitates, presumably the intermediate ruthenium (VI) esters, which easily decomposed during the work-up step.Results from oxidation of trans-7-tetradecene and cis and trans-11-tetradecenyl acetate indicated that the reaction was syn stereospecific.In some cases, 1,3-dioxolane products, formed by condensation of the 1,2-diol and the aldehyde materials, were also obtained among the reaction products.Their possible origin is briefly discussed.