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Kamatham N, Da Silva JP, Givens RS, et al. Melding Caged Compounds with Supramolecular Containers: Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation. Org Lett. 2017;19(13):3588-3591doi: 10.1021/acs.orglett.7b01572.
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
Kamatham, Nareshbabu, et al. "Melding Caged Compounds with Supramolecular Containers: Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation." Organic letters vol. 19,13 (2017): 3588-3591. doi: https://doi.org/10.1021/acs.orglett.7b01572
Kamatham N, Da Silva JP, Givens RS, Ramamurthy V. Melding Caged Compounds with Supramolecular Containers: Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation. Org Lett. 2017 Jul 07;19(13):3588-3591. doi: 10.1021/acs.orglett.7b01572. Epub 2017 Jun 20. PMID: 28631486.
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Org Lett. 2017 Jul 07;19(13):3588-3591. doi: 10.1021/acs.orglett.7b01572. Epub 2017 Jun 20.

Melding Caged Compounds with Supramolecular Containers: Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation.

Organic letters

Nareshbabu Kamatham, José P Da Silva, Richard S Givens, V Ramamurthy

Affiliations

  1. Department of Chemistry, University of Miami , Coral Gables, Miami, Florida 33124, United States.
  2. CCMAR - Centre of Marine Sciences, University of Algarve , Campus de Gambelas, 8005-139 Faro, Portugal.
  3. Department of Chemistry, University of Kansas , Lawrence, Kansas 66045, United States.

PMID: 28631486 DOI: 10.1021/acs.orglett.7b01572

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.

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