Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2020 Mar 5;5(Pt 3):x200288.
doi: 10.1107/S2414314620002886. eCollection 2020 Mar.

1,2,3,5-Tetra-hydro-naphtho-[2,1- c]oxepine

Alan J Lough  1 , Austin Pounder  2 , Christopher Wicks  2 , William Tam  2
Affiliations

1,2,3,5-Tetra-hydro-naphtho-[2,1- c]oxepine

Alan J Lough et al. IUCrdata. .

Abstract

In the title compound, C14H14O, the seven-membered ring is in a pseudo-chair conformation. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds forming layers parallel to (010). In addition, there are weak π-π stacking inter-actions between inversion-related naphthalene ring systems, with a ring centroid-ring centroid distance of 3.518 (5) Å.

Keywords: crystal structure; regioisomer; ring-opening reaction; weak hydrogen bonds.

PubMed Disclaimer

Figures

Figure 1
Figure 1
The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
Figure 2
Figure 2
Part of the crystal structure with weak hydrogen bonds shown as dashed lines. Only H atoms involved in hydrogen bonds are shown.
Figure 3
Figure 3
The reaction scheme.
See this image and copyright information in PMC

References

    1. Bruker (2018). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
    1. Carlson, E., Boutin, R. & Tam, W. (2018). Tetrahedron, 74, 5510–5518.
    1. Carlson, E., Haner, J., McKee, M. & Tam, W. (2014). Org. Lett. 16, 1776–1779. - PubMed
    1. Carlson, E., Hong, D. & Tam, W. (2016). Synthesis, 48, 4253–4259.
    1. Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. - PMC - PubMed

LinkOut - more resources