Osmapyridine and Osmapyridinium from a Formal [4+2] Cycloaddition Reaction

Metalla‐cycloaddition: An unprecedented formal [4+2] cycloaddition reaction takes place when osmium hydrido alkenylcarbyne 1 reacts with acetonitrile to afford the first metallapyridinium complex 2 in high yield (see scheme). Deprotonation of 2 gives the first osmapyridine compound 3. Treatment of 3...

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Published inAngewandte Chemie (International ed.) Vol. 48; no. 30; pp. 5430 - 5434
Main Authors Liu, Bin, Wang, Huijuan, Xie, Hujun, Zeng, Birong, Chen, Jinxiang, Tao, Jun, Wen, Ting Bin, Cao, Zexing, Xia, Haiping
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2009
WILEY‐VCH Verlag
Wiley
Subjects
aromaticity
Chemistry
Chemistry, Multidisciplinary
cycloaddition
metallacycles
osmium
paramagnetism
Physical Sciences
Science & Technology
TRANSFORMATION
ALKYLIDENE
COMPLEX
DIELS-ALDER REACTIONS
paramagnetism
osmium
MULTIPLY SUBSTITUTED PYRIDINES
cycloaddition
SPECTROSCOPY
LIGANDS
NITRILES
CHEMISTRY
aromaticity
metallacycles
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Summary:Metalla‐cycloaddition: An unprecedented formal [4+2] cycloaddition reaction takes place when osmium hydrido alkenylcarbyne 1 reacts with acetonitrile to afford the first metallapyridinium complex 2 in high yield (see scheme). Deprotonation of 2 gives the first osmapyridine compound 3. Treatment of 3 with HBF4 can regenerate 2 in almost quantitative yield.
Bibliography:http://dx.doi.org/10.1002/anie.200900998
This work was financially supported by the National Science Foundation of China (Nos. 20572089, 20872123, and 20873105).
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200900998