Abstract
By merging well-established concepts of supramolecular chemistry, protecting group strategy, and photochemistry, we have solubilized in water hydrophobic organic molecules consisting of a photoactive protecting group and masked carboxylic acids, released the desired acid, and confined a reactive carbocation intermediate within a capsule. Confinement of the photogenerated carbocation brought out the latent radical-like behavior. This observation is consistent with the recent theoretical prediction of the 7-(diethylamino)coumarinyl-4-methyl carbocation having a triplet diradical ground-state electronic contribution.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3588-3591 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 19 |
| Issue number | 13 |
| DOIs | |
| State | Published - Jul 7 2017 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Kamatham, N., Da Silva, J. P., Givens, R. S., & Ramamurthy, V. (2017). Melding Caged Compounds with Supramolecular Containers: Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation. Organic Letters, 19(13), 3588-3591. https://doi.org/10.1021/acs.orglett.7b01572