Display options
Cite
Kancherla S, Lorentzen M, Snieckus V, et al. Directed ortho-Metalation and Anionic ortho-Fries Rearrangement of Polycyclic Aromatic O-Carbamates: Regioselective Synthesis of Substituted Chrysenes. J Org Chem. 2018;83(7):3590-3598doi: 10.1021/acs.joc.7b03210.
Kancherla, S., Lorentzen, M., Snieckus, V., & Jørgensen, K. B. (2018). Directed ortho-Metalation and Anionic ortho-Fries Rearrangement of Polycyclic Aromatic O-Carbamates: Regioselective Synthesis of Substituted Chrysenes. The Journal of organic chemistry, 83(7), 3590-3598. https://doi.org/10.1021/acs.joc.7b03210
Kancherla, Sindhu, et al. "Directed ortho-Metalation and Anionic ortho-Fries Rearrangement of Polycyclic Aromatic O-Carbamates: Regioselective Synthesis of Substituted Chrysenes." The Journal of organic chemistry vol. 83,7 (2018): 3590-3598. doi: https://doi.org/10.1021/acs.joc.7b03210
Kancherla S, Lorentzen M, Snieckus V, Jørgensen KB. Directed ortho-Metalation and Anionic ortho-Fries Rearrangement of Polycyclic Aromatic O-Carbamates: Regioselective Synthesis of Substituted Chrysenes. J Org Chem. 2018 Apr 06;83(7):3590-3598. doi: 10.1021/acs.joc.7b03210. Epub 2018 Mar 20. PMID: 29542919.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2018 Apr 06;83(7):3590-3598. doi: 10.1021/acs.joc.7b03210. Epub 2018 Mar 20.

Directed ortho-Metalation and Anionic ortho-Fries Rearrangement of Polycyclic Aromatic O-Carbamates: Regioselective Synthesis of Substituted Chrysenes.

The Journal of organic chemistry

Sindhu Kancherla, Marianne Lorentzen, Victor Snieckus, Kåre B Jørgensen

Affiliations

  1. Faculty of Science and Technology , University of Stavanger , N-4036 Stavanger , Norway.
  2. Department of Chemistry , Queen's University , 90 Bader Lane , Kingston , Ontario K7L 3N6 , Canada.

PMID: 29542919 DOI: 10.1021/acs.joc.7b03210

Abstract

A general method for the regioselective synthesis of a series of ortho-substituted chrysenyl N, N-diethyl- O-carbamates by the directed ortho-metalation (D oM) strategy is reported. The starting O-carbamates were prepared from the corresponding chrysenols, available by oxidative photochemical cyclization or directed remote metalation tactics. Chrysen-1-yl and chrysene-3-yl ring site selectivity of directed ortho-metalation (D oM) and anionic ortho-Fries rearrangement (A oF) protocols, with s-BuLi/TMEDA, followed by electrophilic quench using a selection of electrophiles, were observed, leading to new chrysenyl derivatives. 5-Chrysenyl N,N-diethyl- O-carbamate underwent instant A oF rearrangement even at -100 °C to furnish chrysenyl o-hydroxycarboxamide. Iterative D oM reactions were carried out to gain insight into the regioselectivity factors.

Publication Types