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9-Azahomocubane.

Authors :
Fahrenhorst-Jones T
Marshall DL
Burns JM
Pierens GK
Van Meurs DP
Kong D
Bernhardt PV
Blanksby SJ
Savage GP
Eaton PE
Williams CM
Source :
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Jan 11; Vol. 30 (3), pp. e202303133. Date of Electronic Publication: 2023 Nov 20.
Publication Year :
2024

Abstract

Homocubane, a highly strained cage hydrocarbon, contains two very different positions for the introduction of a nitrogen atom into the skeleton, e. g., a position 1 exchange results in a tertiary amine whereas position 9 yields a secondary amine. Herein reported is the synthesis of 9-azahomocubane along with associated structural characterization, physical property analysis and chemical reactivity. Not only is 9-azahomocubane readily synthesized, and found to be stable as predicted, the basicity of the secondary amine was observed to be significantly lower than the structurally related azabicyclo[2.2.1]heptane, although similar to 1-azahomocubane.<br /> (© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)

Details

Language :
English
ISSN :
1521-3765
Volume :
30
Issue :
3
Database :
MEDLINE
Journal :
Chemistry (Weinheim an der Bergstrasse, Germany)
Publication Type :
Academic Journal
Accession number :
37823679
Full Text :
https://doi.org/10.1002/chem.202303133