Journal article

Publication year: 2020

Pages: 4441-4447

Journal: The Journal of Organic Chemistry

Volume number: 85

Issue number: 6

ISSN: 0022-3263

DOI Link: https://doi.org/10.1021/acs.joc.0c00167

Publisher: American Chemical Society

Abstract: 
Perhydroazulenes are common structural motifs in various terpene natural products. Herein, we present the synthesis of parent cis- and trans-perhydroazulenes. Conformational analysis performed with density functional theory (DFT, e.g., B3LYP, M06-2X) and MP2 geometry optimizations with a cc-pVTZ basis set, followed by CCSD(T)/cc-pVTZ single-point energy computations reveals that the cis isomer is 0.7 kcal mol(-1) more stable than the trans isomer. Steric and torsional strains present in the trans isomer are responsible for this unexpected relative cis/trans stability.

Harvard Citation style: Saito, F., Becker, J. and Schreiner, P. (2020) Synthesis and Conformational Analysis of Parent Perhydroazulenes Reveal an Energetically Preferred cis Ring Fusion, The Journal of Organic Chemistry, 85(6), pp. 4441-4447. https://doi.org/10.1021/acs.joc.0c00167

APA Citation style: Saito, F., Becker, J., & Schreiner, P. (2020). Synthesis and Conformational Analysis of Parent Perhydroazulenes Reveal an Energetically Preferred cis Ring Fusion. The Journal of Organic Chemistry. 85(6), 4441-4447. https://doi.org/10.1021/acs.joc.0c00167