32362-97-3Relevant articles and documents
One-pot synthesis of 2-alkyl cycloketones on bifunctional Pd/ZrO2 catalyst
Xue, Weiyang,Gu, Bin,Wu, Huiling,Liu, Mengyang,He, Songbo,Li, Jingmei,Rong, Xin,Sun, Chenglin
, (2021/03/26)
2-Alkyl cycloketones are essential chemicals and intermediates for synthetic perfumes and pesticides, which are conventionally produced by multistep process including aldol condensation, separation and hydrogenation. In present work, a batch one-pot cascade approach using aldehydes and cycloketones as the raw materials, and a bifunctional Pd/ZrO2 catalyst was developed for the synthesis of 2-alkyl cycloketones, e.g., cyclohexanone and cycloheptanone. Very high aldehydes (except for paraldehyde with large steric hindrance) conversion and high yields for 2-alkyl cycloketones (e.g., 99 % of conversion for n-butanal and 76 wt.% of yield for 2-butyl cyclohexanone) were obtained at mild temperature of 140 °C. After 10 cycles of reuse, Pd/ZrO2 catalyst showed slight deactivation (ca. 5 % conversion and 10 % yield losses), due to the coke on the catalyst. However, the performance of the catalyst was completely recovered after an oxidative regeneration.
New Method for Generation of β-Oxido Carbenoid via Ligand Exchange Reaction of Sulfoxides: A Versatile Procedure for One-Carbon Homologation of Carbonyl Compounds
Satoh, Tsuyoshi,Itoh, Norifumi,Gengyo, Kaoru,Takada, Sae,Asakawa, Naoyuki,et al.
, p. 11839 - 11852 (2007/10/02)
A new procedure for one-carbon homologation of carbonyl compounds is described.The method is based on the rearrangement of β-oxido carbenoid which is generated via the ligand exchange reaction of the sulfinyl group of α-chloro β-hydroxy sulfoxide with tert-butyllithium.Addition of the carbanion of aryl 1-chloroalkyl sulfoxides to carbonyl compounds gave the adducts in good yields.The β-oxido carbenoid rearrangement of the adducts gave one-carbon homologated carbonyl compounds having an α-alkyl substituent.A similar reaction of the adducts derived from carbonyl compounds with chloromethyl p-tolyl sulfoxide yielded a procedure for a methylene insertion.The stereochemistry of the β-oxido carbenoid rearrangenment is also discussed.
A novel method for generation of carbenoid from α-chloro sulfoxides: A new and versatile procedure for one-carbon homologation of carbonyl compounds to carbonyl compounds having an α-alkyl substituent
Satoh, Tsuyoshi,Itoh, Norifumi,Gengyo, Kaoru,Yamakawa, Koji
, p. 7543 - 7546 (2007/10/02)
Addition of the carbanion of 1-chloroalkyl p-tolyl sulfoxides to carbonyl compound gave the adducts, which were treated with a base followed by t-butyllithium to afford one-carbon homologated carbonyl compounds having an alkyl group at the α-position, via the β-oxido carbenoids, in moderate to good yields.
