syn‐ and anti‐Isomers of a O‐Methyloxime‐Substituted Tricyclic Ozonide

Abstract

The ozonolysis of bicyclo[9.4.0]pentadec-1(11)-en-12-one (4) in pentane, followed by the treatment of the ozonolysis product with O-methylhydroxylamine afforded the stable ozonides anti-(8) and syn-2- O-methyloxime-16,17,18-trioxatricyclo[10.3.2.1]octadecane (9).

Structural characterization of unusually stable polycyclic ozonides

“…As can be seen in Table 2, the oxygen-oxygen bond lengths computed with the semi-empirical PM6 method show higher deviation from the experimental values (2.3-3.8%) than that obtained with the B3LYP/6-31G(d) approach (0.1-1.8%). In general, the O-O bond lengths observed in the X-ray analysis (1.484-1.499 Å) are more elongated than the standard value of 1.47 Å [22]. In the cyclic structures of compounds (3-9) we expected a shorter bond length due to ring tension.…”

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

“…For the ozonolysis of the bicyclic cyclohexenone, 2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1 H -benzo[13]annulen-1-one ( 168 ), two reaction pathways can be proposed through intermediate 169 to form ozonides 170 and 171 . It appeared that the reaction gave only 16,17,18-trioxatricyclo[10.3.2.11,12]octadecan-2-one 171 as two isomers, with the anti isomer in 60% and the syn isomer in 10% yield ( Scheme 43 ) [ 294 ]. The structures of these compounds were established by X-ray diffraction [ 294 ].…”

“…It appeared that the reaction gave only 16,17,18-trioxatricyclo[10.3.2.11,12]octadecan-2-one 171 as two isomers, with the anti isomer in 60% and the syn isomer in 10% yield ( Scheme 43 ) [ 294 ]. The structures of these compounds were established by X-ray diffraction [ 294 ].…”

Facile Synthesis and Preferred Conformation Analysis of Cyclododeceno[b]indene

“…Cyclohexeno[b]indene in particular has been used as a Ziegler-Natta catalyst metal ligand [5]. In another aspect, bi- and tricyclic compounds with bridge double bonds are very useful starting reagents for the synthesis of macrocyclic compounds such as the fragrant macrocyclic lactone pentadecanolide and related compounds [6,7]. Synthesis of indene derivatives containing cyclic olefins ranging from 5 to 12-membered rings have been reported, with the exception of the corresponding 11-membered ring compounds.…”