期刊
ORGANIC LETTERS
卷 25, 期 3, 页码 560-564出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.3c00037560Org
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We report the synthesis and structural study of 2-substituted 1,3-bis(dimethylamino)pentalenes, which exhibit shifted polarized structures due to the electron-donating substituents. Depending on the steric effects, the compounds can adopt planar cyclopentadienyl vinamidiniums or distorted structures mimicking key Breslow intermediates in thiamine-dependent enzymes. This study highlights the use of avoiding anti-aromaticity in accessing unconventional distorted conformations of organic molecules.
We report the synthesis and structural study of 2substituted 1,3-bis(dimethylamino)pentalenes. The two electrons donating substituents shift the formally anti-aromatic pattern toward more suitable polarized structures. A subtle steric trade-off can result either in planar cyclopentadienyl vinamidiniums or in distorted structures featuring a pyramidalized ylidic carbon adjacent to a stabilized pi-conjugated iminium (polymethine). This latter pattern mimics a postulated activated distorted geometry for key Breslow intermediates in the active site of thiaminedependent enzymes. It highlights how the energetic drive to avoid anti-aromaticity can be used to access models for unconventional distorted conformations of organic molecules. [GRAPHICS]
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