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1-Azahomocubane.

ABSTRACT: Highly strained cage hydrocarbons have long stood as fundamental molecules to explore the limits of chemical stability and reactivity, probe physical properties, and more recently as bioactive molecules and in materials discovery. Interestingly, the nitrogenous congeners have attracted much less attention. Previously absent from the literature, azahomocubanes, offer an opportunity to investigate the effects of a nitrogen atom when incorporated into a highly constrained polycyclic environment. Herein disclosed is the synthesis of 1-azahomocubane, accompanied by comprehensive structural characterization, physical property analysis and chemical reactivity. These data support the conclusion that nitrogen is remarkably well tolerated in a highly strained environment.

SUBMITTER: Fahrenhorst-Jones T

PROVIDER: S-EPMC10016339 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

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1-Azahomocubane.

Fahrenhorst-Jones Tyler T Marshall David L DL Burns Jed M JM Pierens Gregory K GK Hormann Robert E RE Fisher Allison M AM Bernhardt Paul V PV Blanksby Stephen J SJ Savage G Paul GP Eaton Philip E PE Williams Craig M CM

Chemical science 20230222 11

Highly strained cage hydrocarbons have long stood as fundamental molecules to explore the limits of chemical stability and reactivity, probe physical properties, and more recently as bioactive molecules and in materials discovery. Interestingly, the nitrogenous congeners have attracted much less attention. Previously absent from the literature, azahomocubanes, offer an opportunity to investigate the effects of a nitrogen atom when incorporated into a highly constrained polycyclic environment. He ...[more]

PMID: 36937576

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