The reactions of 4,4-dimethylspiro[adamantane-2,3'-[ 1,2]-diaxetane] (1a) and biadamantylidene-1, 2-dioxetane (2a) in dichloromethane, at different reaction temperatures, with tris(2,4-dibromophenyl) aminium hexachloroantimonate A afford high yields of the rearranged ketones 2-methyladamantyl-methyl ketone (3) and spiro[adamantane-2,4'-homoadamantan-5'-one] (8), respectively. A cation radical monodeoxygenation process is suggested. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
Monodeoxygenation of spiro adamantane-1,2-dioxetanes induced by aminium salt
FARINOLA, Gianluca Maria;NACCI, Angelo;
1998-01-01
Abstract
The reactions of 4,4-dimethylspiro[adamantane-2,3'-[ 1,2]-diaxetane] (1a) and biadamantylidene-1, 2-dioxetane (2a) in dichloromethane, at different reaction temperatures, with tris(2,4-dibromophenyl) aminium hexachloroantimonate A afford high yields of the rearranged ketones 2-methyladamantyl-methyl ketone (3) and spiro[adamantane-2,4'-homoadamantan-5'-one] (8), respectively. A cation radical monodeoxygenation process is suggested. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.File in questo prodotto:
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