Chemiluminescence (CL) was found during the oxidation of C60 (1) with ozone in solutions of toluene and methylnaphthalene. This CL is more intense (Jmax = 6.2" 109 photon (s mL) -I) than that observed during ozonization of toluene (Jm,x = 7.6" 105 photon (s mL)-l). No chemiluminescence appears upon contact of solutions of I with 0 2. It is most likely that the CL spectrum ( Fig. 1) is mainly due to the emission of diketone O=C60=O *. Photoluminescence (PL) of the products of ozonolysis of 1 is much more intense than the weak PL of fullerene. The maximum PL coincides with krnax = 685 nm of the CL spectrum. The kinetics of consumption of compound 1 and accumulation and consumption of diketones and epoxides C600 n (where n --1--5) during ozonolysis of a toluelae solution of 1 were studied by PL, IR spectroscopy, and HPLC. The data obtained were compared to the kinetic behavior of the CL intensity over time, which has a broad maximum at the fifth ruin. Ketones of fullerene are more stable than epoxides, which decompose 30 rain after the beginning of ozonolysis of I in toluene. The kinetic curves of CL and yield of ketones are parallel. These data coupled with the absence of an influence of ionol inhibitor and the absence of CL at 1270 nm imply the following mechanism of CL. When the O--O bond is cleaved in the intermediate monoozonide, excited diketone (CL emit- ter) and toluene epoxide are formed. The latter is further transformed into cresol with yields higher for ozonolysis of a toluene solution of I than for ozonolysis of toluene (identified by GLC).Received December 30, 1998; in revised form March 25, 1999 New approach to the synthesis of benzoazacrown ethers S. P. Gromov,* A. L Vedernikov, and S. N. Dmitrieva Photochemistry Center, Russian Academy of Sciences, 7A uL Novatorov, 117421 Moscow, Russian Federation. Fax: +7 (095) 936 1255. E-mail: gromov@mx.icp.rssi.nt Until recently, cross-linking of two different fragments has been used as the main approach to the development of macrocycles in the chemistry of macroheterocyclic compounds. !-3 At the same time, for heterocyclic compotmds containing three-and sevenmembered cycles, the following methods for designing
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.