A Pummerer-Type Novel Ring Fission of 2-Methylsulfinyl-5, 6-dihydro-4H-1, 3, 4-thiadiazine Derivatives: A Homologation of Aldehydes and Ketones.

K Shimada, A Otaki, M Yanakawa, S Mabuchi…

Index: Shimada, Kazuaki; Otaki, Akihiro; Yanakawa, Masaki; Mabuchi, Shosuke; Yamakado, Naoya; Shimoguchi, Takeshi; Inoue, Kazuya; Kagawa, Takashi; Shoji, Kazutoshi; Takikawa, Yuji Bulletin of the Chemical Society of Japan, 1996 , vol. 69, # 4 p. 1043 - 1054

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Citation Number: 4

Abstract

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 ...