N-OXIDES OF 2,2'-6',2''-TERPYRIDINE
N-OXIDES OF 2,2'-6',2''-TERPYRIDINE
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DOI：
10.1021/jo00219a043
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发表时间：
1985-01-01
影响因子：
3.6
通讯作者：
JAHNG, Y
中科院分区：
文献类型：
--
作者：
THUMMEL, RP;JAHNG, Y
2，2 ′：6 ′ 2 ″-三联吡啶与30%过氧化氢在80 ℃醋酸溶液中反应，可有效地制备三氮氧化物3（88%）。1在该反应中没有观察到低级N-氧化物。另一方面，使用化学计量量的间氯过苯甲酸作为氧化剂提供单-N-氧化物1，而过量的该试剂得到二-N-氧化物2，两者都完全排除了三-N-氧化物。1和2都可以通过用30%过氧化氢处理转化为3。正如预期的那样，这些物质的极性增加导致其熔点单调增加：1（134-135 C），2（232-233 C）和3（320-321 C dec）。这三种氮氧化物在红外光谱中均在1250 cm-1处显示出非常强的特征性N-0伸缩带。通过热喷雾电离技术获得质谱，其中观察到带正电荷的质子化离子。所有三种氮氧化物
The tri-N-oxide 3 has been efficiently prepared (88%) by the reaction of 2, 2': 6'2"-terpyridinewith 30% hydrogen peroxide in acetic acid at 80 C. 1 None of the lower N-oxides were observed in this reaction. On the other hand, the use of a stoichiometric amount of m-chloroperbenzoic acid as oxidant provides the mono-N-oxide 1 while excess of this reagent gives the di-N-oxide 2, both to the total exclusion of tri-N-oxide. Both 1 and 2 may be converted to 3 by treatment with 30% hydrogen peroxide. As ex-pected, the increasing polarity of these substances leads to a monotonic increase in their melting points: 1 (134-135 C), 2 (232-233 C), and 3 (320-321 C dec). All three N-oxides showed a very intense and charac-teristic N-0 stretchingband at about 1250 cm™ 1 in their infrared spectra. Mass spectra were obtained by the thermospray ionization technique in which the positively charged protonated ions are observed. All three N-oxides