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

doi:10.6023/cjoc201811015

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

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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

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 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.

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

Jiang Wenjie^a,b, Song Yating^a,b, Wei Xiaojing^a, Xu Yi^a, Lu Juan^a, Jiang Bo^a,b, Hao Wenjuan^a

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 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.

1. C—C Triple Bond Cleavage/Rearrangement Reaction for Accessing 2,4,4-Trichloronaphthalen-1(4H)-ones.PDF(4032KB)

Abstract

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

Cite this article

Jiang Wenjie, Song Yating, Wei Xiaojing, Xu Yi, Lu Juan, Jiang Bo, Hao Wenjuan. C—C Triple Bond Cleavage/Rearrangement Reaction for Accessing 2,4,4-Trichloronaphthalen-1(4H)-ones[J]. Chin. J. Org. Chem., 2019, 39(4): 1095-1101.

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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

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

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