What question did this study set out to answer?

Develop a new synthetic pathway to assemble the phenanthrene tricyclic framework using ortho bis(aryne) equivalents and demonstrate its utility in preparing sterically crowded permethylphenanthrene.

November 1, 1981The Journal of Organic Chemistry

New phenanthrene synthesis via ortho bis(aryne) equivalents. Application to permethylphenanthrene

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Authors

HHHarold HartGifu Pharmaceutical University SSShamouil ShamouilianDigital Wave (United States)

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Implication

Chemical synthesis study demonstrates an efficient route to phenanthrenes using ortho bis(aryne) equivalents, highlighting a streamlined approach to crowded polycyclic aromatics.

Key Points

Develop a new synthetic pathway to assemble the phenanthrene tricyclic framework using ortho bis(aryne) equivalents and demonstrate its utility in preparing sterically crowded permethylphenanthrene.
Generated reactive ortho bis(aryne) synthetic equivalents to serve as key building blocks for polycyclic ring construction.
Applied the bis(aryne) cycloaddition methodology to assemble the fully methylated target compound, permethylphenanthrene.
Demonstrated the successful formation of the phenanthrene core structure using ortho bis(aryne) equivalents as dual aryne synthons.
Achieved the direct synthesis of permethylphenanthrene, establishing the utility of this strategy for constructing highly hindered polycyclic aromatic frameworks.

Cite This Study

Hart et al. (1981) studied this question.

synapsesocial.com/papers/6a922bb4cf08077344f0c5e3 https://doi.org/10.1021/jo00337a009

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Implication

Chemical synthesis study demonstrates an efficient route to phenanthrenes using ortho bis(aryne) equivalents, highlighting a streamlined approach to crowded polycyclic aromatics.

New phenanthrene synthesis via ortho bis(aryne) equivalents. Application to permethylphenanthrene

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Implication

Key Points

Cite This Study

New phenanthrene synthesis via ortho bis(aryne) equivalents. Application to permethylphenanthrene

Discussion

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Implication

Key Points

Cite This Study

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