rac-(2a S,2a1 R,3a R,3a1 S,5a S,6a R)-2a-Allyl-2,4-di-chloro-2a,2a1,3a1,5a,6,6a-hexa-hydro-3a H-3-oxadi-cyclo-penta-[ cd, gh]penta-len-3a-ol

Sambasivarao Kotha; Saima Ansari; Naveen Kumar Gupta

doi:10.1107/S2414314621012608

rac-(2a S,2a¹ R,3a R,3a¹ S,5a S,6a R)-2a-Allyl-2,4-di-chloro-2a,2a¹,3a¹,5a,6,6a-hexa-hydro-3a H-3-oxadi-cyclo-penta-[ cd, gh]penta-len-3a-ol

IUCrdata. 2021 Dec 16;6(Pt 12):x211260. doi: 10.1107/S2414314621012608. eCollection 2021 Dec.

Authors

Sambasivarao Kotha¹, Saima Ansari¹, Naveen Kumar Gupta¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India.

Abstract

The title racemic triquinane, C₁₄H₁₄Cl₂O₂, is composed of four five-membered rings, one of which is a tetra-hydro-furan ring to which an allyl group on one side and a hydroxyl group on the other side are attached. The core of the triquinane unit has a cis-syn-cis configuration. In the crystal, the mol-ecules are linked by pairwise O-H⋯O hydrogen bonds, generating inversion dimers featuring R ² ₂(8) loops.

Keywords: crystal structure; hemiketal; indium-catalysed; transannular cyclization; triquinane.

Grants and funding

Funding for this research was provided by: Defence Research and Development Organisation, Aeronautics Research and Development Board (grant No. ARDB/01/104189/M/I to Prof. S Kotha); University Grants Commission (scholarship to Saima Ansari); Council of Scientific and Industrial Research, India (scholarship to Naveen Kumar Gupta).