Crystal structures of 3,6-diallyltetracyclo[6.3.0.0^4,11.0^5,9]undeca-2,7-dione and 1,7-diallylpentacyclo[5.4.0.0^2,6. 0^3,10.0^5,9]undecane-8,11-dione: allylated caged compounds

Abstract

The crystal structures of two allyl­ated caged mol­ecules and the correlation of bond distances and feasibility of ring-closing metathesis is discussed.

Hexacyclo[7.5.1.01,6.06,13.08,12.010,14]pentadecane-7,15-dione

“…2) range from 1.559 (4) to 1.598 (4) Å (Dhaneshwar et al, 1988). However, in the saturated hexacyclic system of (I), the C4-C5 bond is longer, with a value of 1.607 (3) Å , which is unusual among cyclobutane bond lengths but is comparable with the corresponding bond in the related cage molecule 1,7-diallylpentacyclo[5.4.0.0 2,6 .0 3,10 .0 5,9 ]undecane-8,11-dione [1.612 Å ; Kotha et al, 2014]. This may be because the hexacyclic dione system attached to the cyclobutane ring influences the bond length of the fused carbon atoms (C4-C5).…”

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

“…230) [609], 6-O-benzoylzeylenol [610], the cembranoid skeleton [611], cyclohexenes fused to polycycles (two-fold metathesis) (e.g. 231) [612], cyclohexenes that feature spiro fusion to an angular triquinane system [613], cyclohexenes fused to carbohydrate systems [614], and cyclohexenes fused to a naphthalene system for preparation of the core ring system of kosinostatin [615];…”