METACYCLOPHANES AND RELATED COMPOUNDS. 4. HALOGENATIONS OF 8,16-DIALKYL-ANTI-5,13-DI-TERT-BUTYL(2.2)METACYCLOPHAN-1-ENES AND 2,7-DI-TERT-BUTYL-TRANS-10B,10C-DIALKYL-10B,10C-DIHYDROPYRENES
METACYCLOPHANES AND RELATED COMPOUNDS. 4. HALOGENATIONS OF 8,16-DIALKYL-ANTI-5,13-DI-TERT-BUTYL(2.2)METACYCLOPHAN-1-ENES AND 2,7-DI-TERT-BUTYL-TRANS-10B,10C-DIALKYL-10B,10C-DIHYDROPYRENES
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偏环芳烷及相关化合物。
DOI：
10.1002/chin.198242158
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发表时间：
1982
期刊：
影响因子：
--
通讯作者：
T. Yamato
中科院分区：
文献类型：
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作者：
M. Tashiro;T. Yamato
1 Ob, 1 Oc-二氢芘 (20a-c) 由相应的烷基苯分几个步骤制备。 13和20在四氯化碳溶液中用溴溴化，得到2,7-二-Z-丁基-4,5,9,10-四溴-吡喃·-1Ob,1Oc-二烷基-1Ob,1Oc-二氢芘(2)。在沸腾的苯溶液中用碘处理20，得到脱烷基化的化合物2,7-二-Z-丁基芘(28)。在铁粉存在下用溴对 20 进行溴化时也观察到了这种脱烷基作用。然而，在没有Fe粉的情况下，20的溴化没有得到任何产物。还发现13a和20a用氯化碘或氯进行氯化得到进一步氯化的2,7-二-Z-丁基-2,4,5,9,10-六氯反式-10b,1Oc-二甲基-2,7,10b,1Oc-四氢芘(30)。还讨论了标题化合物的卤化反应路径。尽管Boekelheide和他的同事已经制备了[2.2]间环芳-1-烯3'5和反式-10b、1 Oc-二烷基-10b、1 Oc-二氢芘6-12，但从容易获得的化合物出发，其制备路线对于实际目的来说似乎太长。因此，有关这些化合物的化学信息非常有限。
1 Ob, 1 Oc-dihydropyrenes (20a-c) were prepared from the corresponding alkylbenzenes in several steps. The brominationof 13 and 20 with bromine in a carbon tetrachloride solution afforded 2, 7-di-ZerZ-butyl-4, 5, 9, 10-tetrabromo-rranj·-1 Ob, 1 Oc-di-alkyl-1 Ob, 1 Oc-dihydropyrenes (2). Treatment of 20 with iodine in a boiling benzene solution gave thedealkylated compound, 2, 7-di-ZerZ-butylpyrene (28). Such dealkylation was also observed in the bromination of 20 with bromine inthe presence of Fe powder. However, without Fe powder, the bromination of 20 did not give any products. It was also foundthat the chlorination of 13a and 20a with iodine chloride or chlorine afforded the further chlorinated 2, 7-di-ZerZ-butyl-2, 4, 5, 9, 10-hexachlorotrans-10b, 1 Oc-dimethyl-2, 7, 10b, 1 Oc-tetrahydropyrene (30). The reaction pathways of the halogenation of the titled compounds are also discussed.Although [2.2] metacyclophan-1-enes3'5 and trans-10b, 1 Oc-dialkyl-10b, 1 Oc-dihydropyrenes6-12 have been prepared by Boekelheide and his co-workers, their preparativeroutes from easily available compounds seem to be too long for practical purposes. Therefore, chemical information about these compounds is very much limited.