The N-cyclopropylimine-1-pyrroline photorearrangement as a synthetic tool:: Scope and limitations
The N-cyclopropylimine-1-pyrroline photorearrangement as a synthetic tool:: Scope and limitations
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DOI：
10.1021/jo050871x
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发表时间：
2005-08-19
影响因子：
3.6
通讯作者：
Rodríguez, MA
中科院分区：
文献类型：
--
作者：
Soldevilla, A;Sampedro, D;Rodríguez, MA
[图表]提出了N-环丙基亚胺光重排为1-吡咯啉的范围和限制。不同的取代基的反应性的影响，整个环丙烷环和在亚胺的N-环丙基亚胺结构的位置进行了讨论。所观察到的效果解释从计算研究。主要发现涉及（1）1-取代化合物对重排的反应性增强，（2）拥挤的环丙烷缺乏反应性，和（3）该过程的高化学选择性。
[GRAPHICS]The scope and limitations of the photorearrangement of N-cyclopropylimines to 1-pyrrolines are presented. The influence on the reactivity of different substituents throughout the cyclopropane ring and at the iminic position of the N-cyclopropylimine structure is discussed. The observed effects are interpreted from computational studies. The principal findings relate to (1) the enhanced reactivity of 1-substituted compounds toward rearrangement, (2) the lack of reactivity of crowded cyclopropanes, and (3) the high chemoselectivity of the process.