Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 31, Pages 10662-10664Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja103880c
Keywords
-
Categories
Funding
- National Science Foundation [CHE-0957798]
- Direct For Mathematical & Physical Scien [0957798] Funding Source: National Science Foundation
- Division Of Chemistry [0957798] Funding Source: National Science Foundation
Ask authors/readers for more resources
The synthesis of 1,4,7-trimethyloxatriquinane (1), a 3-fold tertiary alkyl oxonium salt, is described. Compound 1 is inert to solvolysis with alcohols, even at elevated temperatures, but undergoes facile substitution with the strongly nucleophilic azide anion. Since an S(N)1 pathway is excluded, the only reasonable mechanistic interpretation for the reaction between 1 and N-3(-) is S(N)2, despite the fact that substitution is occurring at a tertiary carbon center. This finding is supported by computational modeling and a study of the reaction kinetics, and is also consistent with observed solvent and salt effects.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available