An orthomanganation route to 2-substituted derivatives of N-methyl-1, 8-naphthalimide

被引：2
|
作者：
Nicholson, Brian K. [1 ]
Crosby, Paul M. [1 ]
Maunsell, Kieran R. [1 ]
Wyllie, Megan J. [1 ]
机构：
[1] Univ Waikato, Fac Sci & Engn, Dept Chem, Hamilton 3240, New Zealand
来源：
JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2012年 / 716卷
关键词：
Naphthalimide; Cyclometalation; Manganese carbonyl; X-ray crystal structure; Alkyne; ARYL-KETONES; CRYSTAL-STRUCTURE; ARENES; ALKYNES; MANGANATION; COMPLEXES; CHLORIDE; ALKENES;
D O I：
10.1016/j.jorganchem.2012.06.035
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
N-methyl naphthalimide can be readily cyclomanganated at the 2-position, directed by the adjacent amide O atom. Di-cyclomanganation also occurs readily to attach Mn(CO)(4) groups at both 2, 7 positions. An X-ray structure determination of the mono-substituted example confirmed the five-membered metallocyclic ring. Cleavage of the Mn-C bond by HgCl2 or ICl generates 2-substituted HgCl or I derivatives respectively. Reaction of the mono-cyclomanganated N-methyl naphthalimide with phenylacetylene gives an (eta(5)-cyclohexadienyl)Mn(CO)(3) complex where the cyclohexadienyl ring has formed by two PhCCH adding in a formal [2 + 2 + 2] process across the C(1)-C(2) bond of the naphthalimide, breaking the aromaticity of the naphthalene ring as shown by a single crystal structure determination. (C) 2012 Elsevier B.V. All rights reserved.
引用
收藏
页码：49 / 54
页数：6
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