Which is expected to be more stable: methoxy-methyl carbocation $(\ce{CH3-O-CH2+})$ or tropylium $(\ce{C7H7+})$ cation?

I think because oxygen would donate its lone pair so there will be complete octet formed that would make it more stable. Is this argument true and can it be applied everywhere against resonance?

Is it wrong to say tropylium cation is exceptionally stable?

What would be its (tropylium cation) comparison against cyclopropyl cation?

  • $\begingroup$ Tropylium cation is aromatic and aromaticity is generally a greater stabilisation than most other effects, I guess. $\endgroup$ – Soumik Das Feb 13 '19 at 3:00
  • $\begingroup$ It would be better to think of the first species as a methyl-activated carbonyl than a stabilized carbocation. $\endgroup$ – Zhe Feb 13 '19 at 16:31
  • $\begingroup$ Tropilium salts are a real thing, very empirically. $\endgroup$ – Alchimista Feb 14 '19 at 9:31

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