Racemic 7‐oxabicyclo[2.2.1]heptane‐5‐ exo ‐iodo‐6‐ endo ‐hydroxy‐2‐ endo ‐carboxylic acid‐γ‐lactone | Zendy

Smith Graham | Zendy; Bott Raymond C. | Zendy; Jenkins Ian D. | Zendy; Wermuth Urs D. | Zendy

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Racemic 7‐oxabicyclo[2.2.1]heptane‐5‐ exo ‐iodo‐6‐ endo ‐hydroxy‐2‐ endo ‐carboxylic acid‐γ‐lactone

Author(s) -

Smith Graham,

Bott Raymond C.,

Jenkins Ian D.,

Wermuth Urs D.

Publication year - 2001

Publication title -

acta crystallographica section e

Language(s) - English

Resource type - Journals

ISSN - 1600-5368

DOI - 10.1107/s1600536801012661

Subject(s) - substituent , chemistry , lactone , dimer , stereochemistry , hydrogen bond , crystal structure , intermolecular force , heptane , carboxylic acid , molecule , organic chemistry

The crystal structure of the γ‐lactone of racemic 7‐oxabicyclo[2.2.1]heptane‐5‐ exo ‐iodo‐6‐ endo ‐hydroxy‐2‐ endo ‐carboxylic acid has confirmed the position of the lactone bridge as 2–6 and the exo ‐iodo substituent configuration as previously proposed from chemical and 13 C NMR evidence. The iodo substituent is also involved in a short non‐bonding intermolecular interaction [I⋯O 3.289 (5) Å] with the non‐bridging lactone oxygen giving polymeric chains which link weakly hydrogen‐bonded (C—H⋯O) centrosymmetric dimer units.

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