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Chan CK, Tsai YL, Chang MY. Construction of Nitrated Benzo[3.3.1]bicyclic Acetal/Ketal Core via Nitration of o-Carbonyl Allylbenzenes. Org Lett. 2017;19(6):1358-1361doi: 10.1021/acs.orglett.7b00245.
Chan, C. K., Tsai, Y. L., & Chang, M. Y. (2017). Construction of Nitrated Benzo[3.3.1]bicyclic Acetal/Ketal Core via Nitration of o-Carbonyl Allylbenzenes. Organic letters, 19(6), 1358-1361. https://doi.org/10.1021/acs.orglett.7b00245
Chan, Chieh-Kai, et al. "Construction of Nitrated Benzo[3.3.1]bicyclic Acetal/Ketal Core via Nitration of o-Carbonyl Allylbenzenes." Organic letters vol. 19,6 (2017): 1358-1361. doi: https://doi.org/10.1021/acs.orglett.7b00245
Chan CK, Tsai YL, Chang MY. Construction of Nitrated Benzo[3.3.1]bicyclic Acetal/Ketal Core via Nitration of o-Carbonyl Allylbenzenes. Org Lett. 2017 Mar 17;19(6):1358-1361. doi: 10.1021/acs.orglett.7b00245. Epub 2017 Mar 03. PMID: 28257215.
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Org Lett. 2017 Mar 17;19(6):1358-1361. doi: 10.1021/acs.orglett.7b00245. Epub 2017 Mar 03.

Construction of Nitrated Benzo[3.3.1]bicyclic Acetal/Ketal Core via Nitration of o-Carbonyl Allylbenzenes.

Organic letters

Chieh-Kai Chan, Yu-Lin Tsai, Meng-Yang Chang

Affiliations

  1. Department of Medicinal and Applied Chemistry, Kaohsiung Medical University Hospital, Kaohsiung Medical University , Kaohsiung 807, Taiwan.

PMID: 28257215 DOI: 10.1021/acs.orglett.7b00245

Abstract

Intramolecular annulation of o-carbonyl allylbenzenes was achieved to construct novel nitrated [6,6,6]tricycles having an acetal or ketal motif in good yields. The expeditious one-step nitration route provides 4 or 5 new bond formations, including 2 or 3 C-N bonds and 2 C-O bonds. The structural framework of benzobicycle [3.3.1] is confirmed by X-ray crystallographic analysis. A plausible mechanism is proposed.

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