Electrophilic substitution of conjugated eighteen-membered ring systems. Novel conformational effects in mono-substituted [18]annulenes

Abstract
It is shown that [18]annulene can be converted into nitro[18]annulene and acetyl[18]annulene. The nuclear magnetic resonance spectra of the nitro- and acetyl-derivatives exhibit unusual temperature-dependent effects, which are described and explained. Nitration of 1,7,13-tridehydro[18]annulene leads to the corresponding 3-nitro-derivative. The former forms a 1 : 1 π-complex with 1,3,5-trinitrobenzene.

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