Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (4): 1095-1101.DOI: 10.6023/cjoc201811015 Previous Articles     Next Articles

Articles

利用碳碳叁键断裂重组反应合成2,4,4-三氯萘-1(4H)-酮衍生物

蒋文婕a,b, 宋雅婷a,b, 韦晓静a, 徐义a, 陆娟a, 姜波a,b, 郝文娟a   

  1. a 江苏师范大学化学与材料科学学院 徐州 221116;
    b 江苏师范大学敬文书院 徐州 221116
  • 收稿日期:2018-11-10 修回日期:2018-12-07 出版日期:2019-04-25 发布日期:2018-12-21
  • 通讯作者: 姜波 E-mail:jiangchem@jsnu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21602087)、江苏高校品牌专业建设工程基金、江苏省自然科技基金(No.BK20160212)和江苏省青蓝工程资助项目.

CC Triple Bond Cleavage/Rearrangement Reaction for Accessing 2,4,4-Trichloronaphthalen-1(4H)-ones

Jiang Wenjiea,b, Song Yatinga,b, Wei Xiaojinga, Xu Yia, Lu Juana, Jiang Boa,b, Hao Wenjuana   

  1. a School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou 221116;
    b C. W. Chu College, Jiangsu Normal University, Xuzhou 221116
  • Received:2018-11-10 Revised:2018-12-07 Online:2019-04-25 Published:2018-12-21
  • Contact: 10.6023/cjoc201811015 E-mail:jiangchem@jsnu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.21602087),the Top-notch Academic Programs Project of Jiangsu Higher Education Institutions,the Natural Science Foundation of Jiangsu Province (No.BK20160212),and the Qing Lan Project of Jiangsu Education Committee.

N-Chlorosuccinimide (NCS)-mediated[2+2] cycloaddition and C-C triple bond cleavage/rearrangement reaction of yne-allenones and H2O as a nucleophilic reagent enabled the formation of 18 examples of 2,4,4-trichloronaphthalene-1(4H)-one derivatives with 55%~88% yields. The structures of these obtainable products were based on their NMR, IR and HRMS data, among which the structure of product 2e was confirmed by X-ray analysis. This metal-free transformation features mild conditions, simple operation and high reaction yields. It provides an effective and new protocol for the synthesis of trichloro-substituted naphthalene-1(4H)-ones.

Key words: yne-allenones, [2+2] cycloaddition, C-C triple bond cleavage/rearrangement, 2,4,4-trichloronaphthalene-1(4H)-ones