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Citation: ZHANG Baohua, SHI Lanxiang. Regioselective Synthesis of Dibenzo[d, f] [1, 3]dioxepines[J]. Chinese Journal of Applied Chemistry, ;2018, 35(11): 1331-1334. doi: 10.11944/j.issn.1000-0518.2018.11.170429 shu

Regioselective Synthesis of Dibenzo[d, f] [1, 3]dioxepines

ZHANG Baohua ,
SHI Lanxiang ^,

College of Chemical Engineering, Shijiazhuang University, Shijiazhuang 050035, China

Corresponding author: SHI Lanxiang, kedashilanxiang@163.com
Received Date: 27 November 2017
Revised Date: 15 January 2018
Accepted Date: 5 February 2018

Figures(2)

In order to overcome the shortcomings of facile production of dihydroxy diphenyl ethylene by-product in traditional method, dibenzo [d, f][1, 3] dioxepines was synthesized highly regioselectively from a broad range of terminal alkynes with Lewis acidic guanidinium ionic liquid catalyst in 39%~84% yields. The Lewis acidic guanidinium ionic liquid can be reused five times without significantly decrease in catalytic activity.
- guanidinium ionic liquid,
- dibenzo [d, f][1, 3] dioxepine,
- dihydroxybiphenyl,
- terminal alkyneterminal alkyne
1. [1]
  Masters K S, Bihlmeier A, Klopper W. Tethering for Selective Synthesis of 2, 2'-Biphenols:The Acetal Method[J]. Chem Eur J, 2013,19(52):17827-17835. doi: 10.1002/chem.201301969
2. [2]
  Masters K S, Brase S. The Acetal Concept:Regioselective Accesstoortho, ortho-Diphenols via Dibenzo-1, 3-dioxepines[J]. Angew Chem Int Ed, 2013,52(3):866-869. doi: 10.1002/anie.201207485
3. [3]
  Tocco G, Begala M, Delogu G. Indium(Ⅲ) Chloride-catalyzed One Step Synthesis of Some New Dibenzo[d, f] [1, 3] dioxepines and 12H-Dibenzo[d, g] [1, 3] dioxocin Derivatives[J]. Tetrahedron Lett, 2004,45:6909-6913. doi: 10.1016/j.tetlet.2004.07.081
4. [4]
  Tocco G, Begala M, Meli G. Chemoselective Synthesis of New Dibenzo[d, f]-1, 3-dioxepines and 12H-Dibenzo[d, g]-1, 3-dioxocines[J]. Heterocycles, 2007,71:635-645. doi: 10.3987/COM-06-10975
5. [5]
  Piri F, Jafarian H, Rashidi-Ranjbar P. Pd(Ⅱ) and Hg(Ⅱ)-catalyzed Acetalization Reaction[J]. Org Chem:An Indian J, 2007,3(1):07-09.
6. [6]
  Satoh T, Miura M. Topics in Organometallic Chemistry[M]. Chatani N, Ed. Springer:Berlin, Heidelberg, 2008, 24:61-84.
7. [7]
  Yamaguchi M, Arisawa M, Omata K. Ortho-Vinylation Reaction of Phenols with Ethyne[J]. J Org Chem, 1998,63:7298-7305. doi: 10.1021/jo980785f
8. [8]
  Tocco G, Begala M, Meli G. InCl₃ and ZrCl₄ Catalyzed Regioselective Reaction of 2, 2'-Dihydroxybiphenyl with Terminal Alkynes:Synthesis of New Dibenzo[d, f] [1, 3] dioxepines[J]. Tetrahedron, 2008,64:6755-6759. doi: 10.1016/j.tet.2008.05.011
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