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czjdingyi

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[交流] 【求助】检索[2.2]Paracyclophane的合成方法

请大伙帮忙找找[2.2]Paracyclophane的合成方法，Sciencefinder，CA， Beilstein,都行。请将应助结果上传网盘分享。
谢谢了！

[ Last edited by heavence007 on 2009-12-11 at 16:23 ]

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czjdingyi(金币+1,VIP+0): 12-12 11:41

帮你顶顶~

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czjdingyi(金币+6,VIP+0):谢谢 12-12 11:41
chemistryer(金币+1,VIP+0):鼓励交流 12-13 20:46

用2-氟对二甲苯与溴在130～135℃作用得到2-氟-4-甲基溴苄，后者与三甲胺作用得到相应的季铵盐，再用氧化银转换为季铵碱，最后在甲苯中进行季铵碱热分解，即霍夫曼双分子1,6-降解及环化二聚反应制得

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君子当存含垢纳污之量，不可持好洁独行之操。

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czjdingyi(金币+43,VIP+0):Thank you very much! 12-12 11:42
chemistryer(金币+1,VIP+0):鼓励交流 12-13 20:46

比较可行的路线

(i) H2O, ion-exchange resin , (ii) phenothiazine, xylene; Multistep reaction; Otsubo,T. et al.
Synthetic Communications, 1976 ,  vol.  6,  p. 591 - 596
Full Text


With  sodium hydroxide

  Show Experimental Procedure
Montedison S.p.A.
Patent: US4675462 , 1987
Title/Abstract    Full Text

EXAMPLE 1 (Comparative Test)
Into a 1,000 ml flask equipped with a stirrer, a thermometer and a condenser, there were charged:
100 g of an aqueous solution containing 40percent by weight of NaOH (1 mole), and
62.5 g of an aqueous solution at 63.9percent by weight of p-methylbenzyltrimethylammonium chloride (0.2 moles).
Under continuous stirring, the solution was heated by gradually raising the temperature from 22.deg. C. to 120.deg. C.
The NaOH concentration was maintained at 35percent by weight.
The solution was maintained at the boiling temperature for 5 hours.
The resulting (2,2)-paracyclophane was separated from the reaction mass by solubilization in 300 ml of xylene.
To this purpose, xylene was added to the reaction mass and the slurry was maintained at total reflux under stirring for 0.5 hour.
It was filtered at 95.deg. C., the aqueous phase was separated from the organic solution which was repeatedly washed with water and concentrated to small volume.


With  sodium hydroxide

  Show Experimental Procedure
Montedison S.p.A.
Patent: US4795838 , 1989
Title/Abstract    Full Text

With  iodized misch metal in  tetrahydrofuran
1 h; Ambient temperature other metals investigated; Product distribution;
Takahashi, Senji; Mori, Nobuo
Chemistry Letters, 1989 ,  p. 13 - 14
Title/Abstract    Full Text


  22.2%  With  iodized misch metal in  tetrahydrofuran
1 h; Ambient temperature;
Takahashi, Senji; Mori, Nobuo
Chemistry Letters, 1989 ,  p. 13 - 14
Title/Abstract    Full Text


Multi-step reaction with 2 steps
1: 73 percent / NaBH4 / ethanol; tetrahydrofuran / 20 h / 40 °C
2: 1.) isoamyl nitrite, anthranilic acid, 2.) Raney Ni, H2 / 1.) 1,2-dichloroethane, reflux, 4h, 2.) ethanol, reflux, 17-23 h
  View Scheme
Higuchi, Hiroyuki; Misumi, Soichi
Tetrahedron Letters, 1982 ,  vol.  23,  # 52 p. 5571 - 5574
Title/Abstract    Full Text    View citing articles

Chow, Hak-Fun; Low, Kam-Hung; Wong, King Y.
Synlett, 2005 ,  # 14 p. 2130 - 2134

Trahanovsky, Walter S.; Lorimor, Steven P.
Journal of Organic Chemistry, 2006 ,  vol.  71,  # 5 p. 1784 - 1794

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