title: Synthesis of polyfluoroalkyl cyclobutenes from 3-aza-1,5-enynes via an aza-Claisen rearrangement/cyclization cascade.
abstract: A facile synthetic route to access polyfluoroalkyl functionalized cyclobutenes bearing an exo cyclic double bond from 3-aza-1,5-enynes is reported. The reaction proceeds via a thermal aza-Claisen rearrangement to give an allene-imine intermediate; subsequent cyclization affords the cyclobutene core. The kinetics of the transformation of starting material and the intermediate was studied by (1)H NMR spectroscopy, where a consecutive reaction was revealed.
authors: Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, China.
authors: Xiaoyi
authors: X
authors: Xin
authors: Dongping
authors: D
authors: Wang
authors: Fan
authors: F
authors: Wu
authors: Chunxiang
authors: C
authors: Wang
authors: Haolong
authors: H
authors: Wang
authors: Xincheng
authors: X
authors: Li
authors: Boshun
authors: B
authors: Wan
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D003500:Cyclization; D003503:Cyclobutanes / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000480:Alkynes; D001372:Aza Compounds; D003503:Cyclobutanes; D006845:Hydrocarbons, Fluorinated; D007097:Imines