132610-21-0Relevant articles and documents
Amide Bond Formation Assisted by Vicinal Alkylthio Migration in Enaminones: Metal- and CO-Free Synthesis of α,β-Unsaturated Amides
Liu, Zhuqing,Huang, Fei,Wu, Ping,Wang, Quannan,Yu, Zhengkun
, p. 5731 - 5750 (2018/05/14)
Amide bond formation is one of the most important transformations in organic synthesis, drug development, and materials science. Efficient construction of amides has been among the most challenging tasks for organic chemists. Herein, we report a concise m
Acid Catalyzed Ring Opening of β-Bis(methylthio)methylenealkyl Cyclopropyl Ketones: A Novel Approach to Substituted Cyclopentanones
Deb, Biswajit,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
, p. 2728 - 2758 (2007/10/02)
The bis(methylthio)methylenealkyl cyclopropyl ketones (2) undergo ring opening and subsequent cyclization in the presence of a variety of acid catalysts to give 3-arylcyclopentanone (3), 5-aryl-2-oxocyclopentanecarbothioates (4) and 2-bis(methylthio)methylene-3-arylcyclopentanones (5) in good yields.The open chain carbinols (9) and (10) could also be isolated under controlled conditions in few cases.The cyclization of (2) to cyclopentanone is shown to depend on aryl ring substituents.The mechanistic studies of this cyclization are consistent with the formation of benzyl cation (13) or cyclic oxonium ion intermediate (14).A propable mechanism involving these intermediates for the formation of all these products is suggested.
ACID CATALYZED RING OPENING OF α-BIS(METHYLTHIO)METHYLENEALKYL CYCLOPROPYL KETONES: AN INTRAMOLECULAR ALKYLATION APPROACH TO SUBSTITUTED CYCLOPENTANONES
Deb, B.,Asokan, C.V.,Ila, H.,Junjappa, H.
, p. 2111 - 2114 (2007/10/02)
α-Bis(methylthio)methylenealkyl cyclopropyl ketones 4, prepared by the addition of dimethyloxosulphonium methylide to the respective α-cinnamoylketene dithioacetals 3, undergo facile acid catalyzed intramolecular cyclization with participation of bis(meth
