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Citation: LIANG Ya, LIU Xiu-Ming, CHEN Su-Zhan, WEI Rong-Bao. Synthesis of 9,9'-(1,4-Phenylene) tetra-decahydro diacridine-1,1',8,8'-tetra-one ketal dipentaerythritol[J]. Chinese Journal of Applied Chemistry, ;2007, 24(6): 619-622. shu

Synthesis of 9,9'-(1,4-Phenylene) tetra-decahydro diacridine-1,1',8,8'-tetra-one ketal dipentaerythritol

1.
College of Biotechnology & Chemical Engineering, Tianjin University of Technology, Tianjin 300191

Corresponding author: LIANG Ya,
Received Date: 1 August 2006
Available Online: 30 January 2007
Fund Project: 国家自然科学基金(20472064) (20472064)天津市自然科学基金(040004311) (040004311)金属及分子基材料化学天津市重点实验室(南开大学)开放基金(0002)资助项目 (南开大学)开放基金(0002)

This article describes the synthesis of 9,9'-(1,4-phenylene)-2H,2'H,3H,3'H,4H,4'H,5H,5'H,6H,6'H,7H,7'H,9H,9'H-tetradecahydro-dixanthene-1,1',8,8'-tetra-one (compound Ⅰ) from 1,3-cyclohexedione and 1,4-benzenedicarboaldehyde through condensation and dehydration in acidic medium.The reaction mechanism was proposed.And then,the cyclization reaction between Ⅰ and pentaerythritol gave 9,9'-(1,4-phenylene)-2H,2H,2'H,2'H,3H,3H,3'H,3'H,4H,4H,4'H,4'H,5H,5H,5'H,5'H,6H,6H,6'H,6'H,7H,7H,7'H,7'H,9H,9'H-tetradecahydro dixanthene-1,1',8,8'-tetraone ketal di-pentaerythritol (compound Ⅱ) using I₂ as a catalyst,and the yield was 40%.The structures of Ⅰ and Ⅱ were confirmed by IR,¹H NMR,and MS.In ¹H NMR spectra,the peaks for the eight hydrogen atoms of the methylene groups in compound Ⅱ containing spiro-structure split into four doublets due to the presence of chiral axis and benzene ring.The reaction parameters and the formation of by-products were discussed.
- terephthaldehyde,
- pentaerythritol,
- spiro-compound,
- cyclohexedione
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