Publication Date:
2014-10-26
Description:
The title compounds, C17H20O2 (1) and C17H18O2 (2), are allylated caged compounds. In (1), the carbon atoms bearing the allyl groups are far apart [2.9417 (17) Å], hence the expected ring-closing metathesis (RCM) protocol failed to give a ring-closing product. When these carbon atoms are connected by a C—C bond as in (2), the distance between them is much smaller [1.611 (3) Å] and consequently the RCM process was successful. The caged carbon skeleton of (1) can be described as a fusion of four five-membered rings and one six-membered ring. All four five-membered rings exhibit envelope conformations. The structure of compound (2) consists of four five-membered rings, of which two are cyclopentanone rings bonded at the 2, 4 and 5 positions and linked at the 3-carbons by a methylene bridge. It also consists of one four-membered and two six-membered rings. All four five-membered rings adopt envelope conformations. In the crystal of (1), molecules are linked via C—H...O hydrogen bonds, forming sheets lying parallel to (010). In the crystal of (2), molecules are linked via C—H...O hydrogen bonds forming chains along [100].
Keywords:
Crystal structurecaged compoundspentacyclo [5.4.0.02,6.03,10.05,9]undecane (PCUD)ring-closing metathesis (RCM)Diels–Alder reaction[2 + 2] cycloadditionscrystal structure
Electronic ISSN:
1600-5368
Topics:
Chemistry and Pharmacology
,
Geosciences
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