Synthesis and characterization of macrocyclic polyaza(2,5)pyridinophanes possessing vitamin B6 functionality.
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概要
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Series of macrocyclic polyaza[<I>m</I>](2,5)pyridinophanes (poly=tri, tetra, penta; <I>m</I>=9, 12, 15)(<B>8–10</B>) and polyaza[<I>m</I>]paracyclophanes (<B>11–13</B>) were synthesized in excellent yields by the reaction of dichloropyridoxine derivatives (<B>4</B>) and α,α′-dibromo-<I>p</I>-xylene (<B>5</B>), respectively, with a series of 1,2-ethanediamine derivatives (<B>1–3</B>). These phanes were characterized on the basis of <SUP>1</SUP>H NMR spectra. The methyl group at C<SUB>6</SUB> of the pyridoxine moiety (<B>a</B>-series) revealed restricted rotation for all bridge sizes (<I>m</I>=9–15). In <B>8–10</B> without the methyl group (<B>b</B>-series), <I>m</I>=12 was the boundary between restricted and free rotation. In series <B>11–13</B>, only <B>11</B> (<I>m</I>=9) showed restricted rotation. Atomic group equivalence was discussed in terms of boundary restricted rotation and an empirical rule for the prediction of the relationship between the bridge size and restricted rotation was proposed.
- 公益社団法人 日本化学会の論文
著者
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Kuzuhara Hiroyoshi
RIKEN (The Institure of Physical and Chemical Research)
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Iwata Masaaki
RIKEN (The Institute of Physical and Chemical Research)
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