Journal of the Chemical Society. Perkin transactions I p. 1006 - 1012 (1981)
Update date:2022-09-26
Topics:
Birch, Arthur J.
Kelly, Lawrence F.
Thompson, David J.
Tricarbonylcyclohexadienyliumiron cations can be regarded as synthetic equivalents, depending on the reaction sequence, either of specific aryl cations or, in the case of methoxy-derivatives, of cations derived from cyclohex-2-enones.An important series can be entered through the symmetrical 3-methoxy cation (32, R1 = R2 = H, R3 = OMe) made efficiently for the first time from tricarbonyl-1,3-dimethoxycyclohexa-1,3-dieneiron (18).It is synthetically equivalent to a meta-methoxy-benzene cation or to a 5-cation of cyclohex-2-enone.Another series of aromatic equivalents can be defined based on nucleophilic reactions at the 1-position of derivatives of tricarbonylcyclohexa-2,4-dienoneiron (33), and efficient syntheses of (33) and its 3-methoxy (35) and 4-methoxy (37) derivatives are described.The precursors for these reactions require the efficient complexation of the 1,3- or 1,4-dimethoxycyclohexadienes, which can be carried out using the conjugated, but not the unconjugated, 1,4-dienes where loss of OMe occurs.Related processes are described in preparations and uses of complexes of some 1-morpholinocyclohexa-1,3-dienes.Some mechanisms are discussed.
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