CYCLIZATION OF N-HALOGENATED AMINES (HOFMANN-LOFFLER REACTION
CYCLIZATION OF N-HALOGENATED AMINES (HOFMANN-LOFFLER REACTION
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DOI：
10.1021/cr60221a004
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发表时间：
1963-01-01
期刊：
影响因子：
62.1
通讯作者：
WOLFF, ME
中科院分区：
文献类型：
--
作者：
WOLFF, ME
着手合成、降解或修饰有机结构的化学家通常会根据化合物的官能团性质来评价该化合物的化学性质。这种方法是有效的，因为脂肪族和脂环族链的惰性性质。用于烃异构化的高温和催化方法是广泛使用的工业方法，但是这些方法太剧烈或者不适合用于大多数多官能化合物。虽然传统的离子有机反应只发生在有机化合物的功能位或活化位，但自由基反应却不是这样。自由基通常优先攻击惰性亚甲基而不是活性位置，但正是这一性质导致了多取代产物的混合物。看来，自由基反应适用于预先选定的未活化的烃基的改性，这在合成有机化学中是很有用的，值得注意的是，这种反应，已知的四分之三的世纪，只得到很少的开发。
The chemist who sets out to synthesize, degrade or modify an organic structure customarily appraises the chemistry of that compound in terms of the properties of its functional groups. Such an approach is effective because of the inert nature of aliphatic and alicyclic chains. High temperature and catalytic methods for the isomerization of hydrocarbons are extensively employed industrial processes, but these procedures are too drastic or otherwise unsuitable for use with most polyfunctional compounds. Although conventional ionic organic reactions specifically occur at functional or otherwise activated positions in organic compounds, this is notthe case in free radical reactions. Free radicals often attackinert methylene groups in preference to activated positions, but this very property gives rise to mixtures of polysubstituted products. It would appear that free radical reactions suitable for use in the modifi-cation of pre-selected, unactivated hydrocarbon groups would be of major utility in synthetic organic chemis-try, and it is a remarkable factthat such a reaction, known for three quarters of a century, has received only minor exploitation.