Bleach/acetic acid-promoted chlorinative ring expansion of [2.2.1]- and [2.2.2]-bicycles.

Bleach/acetic acid-promoted chlorinative ring expansion of [2.2.1]- and [2.2.2]-bicycles.
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DOI:
10.1021/ol0267331
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发表时间:
2002-10
期刊:
影响因子:
5.2
通讯作者:
E. Ruggles;R. Maleczka
E. Ruggles;R. Maleczka
中科院分区:
化学1区
文献类型:
--
作者:
E. Ruggles;R. Maleczka

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[公式:用NaOCl和AcOH处理乙烯基取代的[2.2.1]-和[2.2.2]-双环甲醇,分别得到[3.2.1]-和[3.2.2]-β-氯-双环酮。对于[2.2.2]-自行车,这些氯化环扩张特别有效和选择性。
[formula: see text] Treatment of vinyl-substituted [2.2.1]- and [2.2.2]-bicyclocarbinols with NaOCl and AcOH provides [3.2.1]- and [3.2.2]-beta-chloro-bicycloketones, respectively. For [2.2.2]-bicycles, these chlorinative ring expansions are particularly efficient and selective.