(2 R,3 R)-1,4-Dioxa-spiro-[4.4]nonane-2,3-di-carb-oxy-lic and (2 R,3 R)-1,4-dioxa-spiro-[4.5]decane-2,3-di-carb-oxy-lic acids

Mikhail E Minyaev; Dmitrii M Roitershtein; Alexey A Vinogradov; Ivan V Ananyev; Ilya E Nifant'ev

doi:10.1107/S2056989018009593

(2 R,3 R)-1,4-Dioxa-spiro-[4.4]nonane-2,3-di-carb-oxy-lic and (2 R,3 R)-1,4-dioxa-spiro-[4.5]decane-2,3-di-carb-oxy-lic acids

Acta Crystallogr E Crystallogr Commun. 2018 Jul 6;74(Pt 8):1058-1062. doi: 10.1107/S2056989018009593. eCollection 2018 Aug 1.

Authors

Mikhail E Minyaev¹, Dmitrii M Roitershtein^{1

2}, Alexey A Vinogradov¹, Ivan V Ananyev³, Ilya E Nifant'ev^{1

4}

Affiliations

¹ A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 29 Leninsky Prospect, 119991, Moscow, Russian Federation.
² N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow, 119991, Russian Federation.
³ A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova Str., Moscow, 119991, Russian Federation.
⁴ Chemistry Department, M.V. Lomonosov Moscow State University, 1 Leninskie Gory Str., Building 3, Moscow, 119991, Russian Federation.

Abstract

The title compounds, C₉H₁₂O₆ and C₁₀H₁₄O₆, were formed by careful hydrolysis of the corresponding diethyl esters. Their single crystals were grown from an ethyl acetate/hexane mixture. Crystals of both compounds have monoclinic (P2₁) symmetry with a single mol-ecule in the asymmetric unit. Both crystal structures are very similar and display four -CO-OH⋯O=C(OH)- hydrogen bonds, forming a two-dimensional double-layered framework.

Keywords: 1,3-dioxolane; NMR; crystal structure; hydrogen bonding; ketals; tartric acid.

Grants and funding

This work was funded by Russian Academy of Sciences grant .