Selective synthesis of novel cyclic phenylazomethine trimers

被引：49

作者：

Higuchi, M ^{[1
]}

Kimoto, A ^{[1
]}

Shiki, S ^{[1
]}

Yamamoto, K ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Chem, Yokohama, Kanagawa 2238522, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 18期

关键词：

D O I：

10.1021/jo000509c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel cyclic phenylazomethine trimers (CPAs) were synthesized in a one-step dehydration of the 4-aminobenzophenone derivatives in the presence of TiCl4 or p-toluenesulfonic acid (PTS). The CPAs were isolated in over 90% yield under nondilute conditions. When using TiCl4 as the dehydration agent, the induction of bulky substituents at the alpha-position of the substrate enhanced the yields of the CPAs. On the other hand, PTS served as an effective catalyst for the synthesis of the phenyl-substituted CPA. This different reactivity between TiCl4 and PTS depends on the dehydration mechanism being dominated by a kinetic process or thermodynamic one. The obtained CPAs were confirmed by NMR, UV-vis spectra, and MM2 calculation to have only a Z conformation and a nonconjugated structure compared to the Linear oligophenylazomethines (OPAs) and the aniline-capped OPAs (OPA's).

引用

页码：5680 / 5684

页数：5

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