Open Access
Synthesis of 2-Azaadamantan-6-one: A Missing Isomer
Jianbo Wu
1
,
Derek A Leas
1
,
Yuxiang Dong
1
,
Xiaofang Wang
1
,
Edward L. Ezell
1
,
Douglas E Stack
2
,
Jonathan L. Vennerstrom
1
Publication type: Journal Article
Publication date: 2018-09-18
scimago Q1
wos Q2
SJR: 0.773
CiteScore: 7.1
Impact factor: 4.3
ISSN: 24701343
PubMed ID:
30288462
General Chemistry
General Chemical Engineering
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.
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Metrics
6
Total citations:
6
Citations from 2025:
2
(33.33%)
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GOST
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Wu J. et al. Synthesis of 2-Azaadamantan-6-one: A Missing Isomer // ACS Omega. 2018. Vol. 3. No. 9. pp. 11362-11367.
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Wu J., Leas D. A., Dong Y., Wang X., Ezell E. L., Stack D. E., Vennerstrom J. L. Synthesis of 2-Azaadamantan-6-one: A Missing Isomer // ACS Omega. 2018. Vol. 3. No. 9. pp. 11362-11367.
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RIS
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TY - JOUR
DO - 10.1021/acsomega.8b01819
UR - https://doi.org/10.1021/acsomega.8b01819
TI - Synthesis of 2-Azaadamantan-6-one: A Missing Isomer
T2 - ACS Omega
AU - Wu, Jianbo
AU - Leas, Derek A
AU - Dong, Yuxiang
AU - Wang, Xiaofang
AU - Ezell, Edward L.
AU - Stack, Douglas E
AU - Vennerstrom, Jonathan L.
PY - 2018
DA - 2018/09/18
PB - American Chemical Society (ACS)
SP - 11362-11367
IS - 9
VL - 3
PMID - 30288462
SN - 2470-1343
ER -
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BibTex (up to 50 authors)
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@article{2018_Wu,
author = {Jianbo Wu and Derek A Leas and Yuxiang Dong and Xiaofang Wang and Edward L. Ezell and Douglas E Stack and Jonathan L. Vennerstrom},
title = {Synthesis of 2-Azaadamantan-6-one: A Missing Isomer},
journal = {ACS Omega},
year = {2018},
volume = {3},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/acsomega.8b01819},
number = {9},
pages = {11362--11367},
doi = {10.1021/acsomega.8b01819}
}
Cite this
MLA
Copy
Wu, Jianbo, et al. “Synthesis of 2-Azaadamantan-6-one: A Missing Isomer.” ACS Omega, vol. 3, no. 9, Sep. 2018, pp. 11362-11367. https://doi.org/10.1021/acsomega.8b01819.