Abstract
The title compounds, C17H20O2 (1) and C17H18O2 (2), are allyl-ated 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 cyclo-penta-none rings bonded at the 2, 4 and 5 positions and linked at the 3-carbons by a methyl-ene 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), mol-ecules are linked via C-H⋯O hydrogen bonds, forming sheets lying parallel to (010). In the crystal of (2), mol-ecules are linked via C-H⋯O hydrogen bonds forming chains along [100].
Highlights
The title compounds, C17H20O2 (1) and C17H18O2 (2), are allylated caged compounds
[2.9417 (17) Å], 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]
In the crystal of (1), molecules are linked via C—H O hydrogen bonds, forming sheets lying parallel to (010)
Summary
Caged molecules are much sought after chemical entities due to their diverse applications such as high-energy materials, drug intermediates and starting materials for complex natural products (Marchand, 1989a,b; Mehta & Srikrishna, 1997). We report on the crystal structures of the title doi:10.1107/S1600536814023149. These compounds, and their reactions mentioned in this article, are known in the literature (Kotha et al, 1999, 2006) but their crystal structures have not previously been reported. When diallyl tetracyclic dione (1) was subjected to ringclosing metathesis (RCM), the expected ring-closing product (3) was not obtained, Fig. 1. Successfully underwent RCM to yield the desired ring-closing product (4), see Fig. 1. When compound (1) was subjected to cross metathesis (CM) with but-2-ene-1,4-diallyl acetate (7) in the presence of Grubbs catalyst (Fig. 2), the diacetate (5) was formed in 55% yield.
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