Syntheses and relative stability of (D3)-trishomocubane (pentacyclo[6.3.0.02,6.03,10.05,9]undecane), the pentacycloundecane stabilomer

Abstract

Syntheses and Relative Stability of (D3)‐Trishomocubane (Pentacyclo= (6,3,O,O2,5,O3,10,O5,9)undecane), the Pentacycloundecane Stabilomer.

Cage-Shaped Molecules Derived by Applying the Edge Strategy to a Cubane Skeleton

“…Synthesis and absolute configuration of optically active C 2 -bishomocubane 6 have been reported [17]. [18] and by Kent et al [10]. The absolute configuration of (−)D 3 -trishomocubane 17 has been determined by Helmchen and Staiger [11], while the absolute configuration of (+)D 3 -trishomocubane 17 has been determine d by Nakazaki et al [12].…”

“…The present article is devoted to the application of the edge strategy to a cubane skeleton of o h -symmetry, because cubane itself [7] and its derivatives such as basketane [8,9] and D 3 -trishomocubane [10][11][12] have attracted the interest of synthetic organic chemists, as summarized in a review [13]. Although systematic discussions based on D 3 -twisted bicyclo[2.2.2]octane molecular framework as a common structural unit have appeared [14], the edge strategy applied to a cubane skeleton aims at providing more quantitative perspectives.…”

8-Pentacyclo[6.3.0.02,6.03,10.05,9]undec-3'-yl-exo-pentacyclo[5.4.0.02,6.03,10.05,9]undecane

“…Trishomocubane (3) can be described as a fusion of six five-membered rings. Trishomocubane is calculated by molecular mechanics (Allinger, Yuh & Lii, 1989;Technical Utilization Corporation, 1992) to be less strained than PCU [AHf = 6.30 and 3.50 kJ for (2) and (3), respectively] and is formed via a carbenium-ion rearrangement of (2) (Kent, Godleski, Osawa & Schleyer, 1977;Dekker, Oliver & Venter, 1980). lization Corporation, 1992;Sim & Sutton, 1973).…”

A Convenient Road to 1‐Chloropentacycloundecanes – A Joint Experimental and Computational Investigation

“…Kukhar and coworkers [27][28][29][30] and Kent [31] have synthesized a number of 1-substituted D 3 -trishomocubanes [1-hy- ]-undecane-2,7-dione (5), usually in harsh environments or with low yields (Scheme 1).…”