Synthesis of 2-Azaadamantan-6-one: A Missing Isomer

Jianbo Wu, Derek A. Leas, Yuxiang Dong, Xiaofang Wang, Edward L. Ezell, Douglas E. Stack, Jonathan L. Vennerstrom

Research output: Contribution to journalArticle

Abstract

2-Azaadamantan-6-one and its Boc and ethylene ketal derivatives were synthesized from 9-oxo endo-bicyclo[3.3.1]non-6-ene-3-carboxylic acid. Similarly, the Cbz, Boc, and ethylene ketal derivatives of 2-azaadamantan-4-one were synthesized from endo-bicyclo[3.3.1]non-6-ene-3-carboxylic acid. Key steps were Curtius rearrangements to form benzyl carbamates, followed by spontaneous intramolecular attack of the carbamate nitrogen on transient bromonium ion or epoxide intermediates to effect ring closure to azaadamantane intermediates. The reaction sequence leading to 2-azaadamantan-6-one is consistent with the formation of a transient tetracyclic keto aziridine intermediate.

Original languageEnglish (US)
Pages (from-to)11362-11367
Number of pages6
JournalACS Omega
Volume3
Issue number9
DOIs
StatePublished - Sep 30 2018

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Carbamates
Carboxylic Acids
Carboxylic acids
Isomers
Ethylene
Derivatives
Epoxy Compounds
Nitrogen
Ions
ethylene
aziridine

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Synthesis of 2-Azaadamantan-6-one : A Missing Isomer. / Wu, Jianbo; Leas, Derek A.; Dong, Yuxiang; Wang, Xiaofang; Ezell, Edward L.; Stack, Douglas E.; Vennerstrom, Jonathan L.

In: ACS Omega, Vol. 3, No. 9, 30.09.2018, p. 11362-11367.

Research output: Contribution to journalArticle

Wu, Jianbo ; Leas, Derek A. ; Dong, Yuxiang ; Wang, Xiaofang ; Ezell, Edward L. ; Stack, Douglas E. ; Vennerstrom, Jonathan L. / Synthesis of 2-Azaadamantan-6-one : A Missing Isomer. In: ACS Omega. 2018 ; Vol. 3, No. 9. pp. 11362-11367.
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AU - Ezell, Edward L.

AU - Stack, Douglas E.

AU - Vennerstrom, Jonathan L.

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