FIELD: organic synthesis. SUBSTANCE: 1-chloro-3-acetyl- and 1-chloro-1,3- diacetyladamantanes useful as intermediates in synthesis of a series of 1,3- disubstituted and 1,3,5-trisubstituted adamantanes are prepared by chlorination of 1- acetyladamantane by carbon tetrachloride catalyzed by manganese complexes such as MnSO4, MnCl2, Mn(C17H35CO2)2 (stearate), Mn(OAc)2, Mn(acac)3, activated by nitrile ligands (CH3CN, CH3CH2CN, PhCN, CH2(CN)2) for 10-3 h at 200 C and molar ratio [Mn] /[RCN] /[1-acetyladamantane]/[CCl4] = 1:(2-4) : 1000:(1500-5000). Conversion of 1-acetyladamantane is ~ 100% and yield of desired products 98 and 92%, respectively. EFFECT: expanded synthetic possibilities in adamantine series. 1 tbl, 2 ex
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Authors
Dates
2003-01-27—Published
2000-11-09—Filed