Acid-catalyzed cyclization of 3,3',4,4'-tetrahydro-1,1'-binaphthyl and single-crystal x-ray structure determination of a polycyclic stable ozonide

Abstract

Amberlyst-15 (A-15) catalyzed cyclization of 3,3',4,4'-tetrahydro-l,T-binaphthyl (1) in refluxing toluene during 12 h provided, as the major product, (±)-l,2,3,6b,7,8-hexahydrobenzo[/]fluoranthene (2a). Ozonization of 2a gave a stable ozonide (3), mp 159-161 °C. The structure of this ozonide was established by single-crystal X-ray analysis: monoclinic unit cell P^ifc, a = 10.616 (1) A, b = 9.607 (3) A, c = 15.052 (4) A, d = 105.06 (2)°, ]cd 1.372 g cm"1, Z = 4, final agreement factor 6.3%. Prolonged treatment (12-100 h) of 1 or 2a with A-15 in refluxing toluene yielded a mixture of three l,2,3,6b,7,8,12b,12c-octahydrobenzoL/]fluoranthenes (4a, 4b, 4c) and l,2,3,12c-tetrahydrobenzo[/]fluoranthene (5). Hydrocarbon 2a was readily dehydrogenated in the presence of hot Pd/C to benzo[/]fluoranthene (6).Acid-catalyzed cyclization of S.S'^^'-tetrahydro-l.Tbinapthyl (1, Scheme I) for 12 h using Amberlyst-15 (A-15)2 in refluxing toluene provided, as the major product, a C2oH28 olefin which was thought to be 1,2,3,6b,7,8hexahydrobenzo[/]fluoranthene (2a) or 1,2,3,7,8,12chexahydrobenzo [/] fluoranthene (2b).

High capacity mercury adsorption on freshly ozone-treated carbon surfaces

“…5II is a reaction intermediate that decays to a secondary ozonide, which in turn reacts with water to form hydrogen peroxide and ketones [25]. Many secondary ozonides are fleeting intermediates, while others are sufficiently metastable to be isolated and characterized [27][28][29], including ozonides from polycyclic compounds [28,29], which are relatives of graphenic carbon.…”