172472-06-9Relevant academic research and scientific papers
A Pummerer-Type Novel Ring Fission of 2-Methylsulfinyl-5,6-dihydro-4H-1,3,4-thiadiazine Derivatives: A Homologation of Aldehydes and Ketones
Shimada, Kazuaki,Otaki, Akihiro,Yanakawa, Masaki,Mabuchi, Shosuke,Yamakado, Naoya,Shimoguchi, Takeshi,Inoue, Kazuya,Kagawa, Takashi,Shoji, Kazutoshi,Takikawa, Yuji
, p. 1043 - 1054 (2007/10/03)
Aldehydes and ketones were converted into 2-methylsulfinyl-5,6-dihydro-4H-1,3,4-thiadiazines via the formation and base-induced ring-closure of N-alkylidene-N′-bis(alkylthio)methylenehydrazines followed by mCPBA oxidation. The subsequent Pummerer-type ring fission of the rings was performed by treating with trifluoroacetic anhydride or trifluoromethanesulfonic anhydride at -78°C to give α,β-unsaturated esters and ketones in modest yields. Thus, this reaction sequence was regarded as being a new method for the two-carbon homologation of aldehydes and ketones.
A Homologation of Aldehydes and Ketones via the Formation and the Subsequent Pummerer-type Ring Fission of 2-Methylsulfinyl-5,6-dihydro-4H-1,3,4-thiadiazine Derivatives
Shimada, Kazuaki,Otaki, Akihiro,Yanakawa, Masaki,Mabuchi, Shosuke,Yamakado, Naoya,et al.
, p. 925 - 926 (2007/10/03)
A two-carbon homologation of aldehydes and ketones was achieved by using a sequence involving the formation and the subsequent Pummerer-type ring fission of 5,6-dihydro-4H-1,3,4-thiadiazine rings possessing methylsulfinyl functionality at C-2.
