4,10-Diallyloxy-1,2,3,6b,7,8,9,12b-octahydroperylene

Abstract

In the title compound, C26H28O2, the central atoms are coplanar, with the –CH2—CH2– links of the cyclo­hexene groups lying to either side of the plane and with the diall­yloxy residues twisted out of this plane [C—C—O—C torsion angles = 16.6 (3) and −13.9 (3)°]. In the crystal structure, mol­ecules are connected into chains propagating in [100] via C—H⋯π inter­actions.

Synthesis ofcis‐ andtrans‐Configured Octahydroperylenes

“…[10] A 59 % yield was achieved within 30 min when hafnium(IV) triflate was used. [11] Calculation of the possible diastereoisomers of 6 (vide infra) revealed a thermodynamic preference for the desired cis product. Scheme 1.…”

“…This was improved to 62 % by using boron trifluoride-diethyl ether according to a method reported by Penick et al [11] Nevertheless, a longer reaction time of 20 h was needed for this variation. Thus, we were surprised to see that a published X-ray crystallographic analysis of the 4,10-diallyloxy derivative of 3 [11] and also a structural analysis of 6 carried out by us [12] both showed a trans arrangement of the hydrogen atoms at the 6b-and 12bpositions ( Figure 2). Synthesis of dimethoxyoctahydroperylene.…”