I know that cyclopropyl methyl carbocation is exceptionally stable compared to say, benzyl carbocation.

But I want to know how stable is cyclobutyl methyl carbocation compared to say, tertiary/secondary carbocations? Or, will it go rearrangement breaking the ring?

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    $\begingroup$ DOI: 10.1021/ja01473a028 <BR> DOI: 10.1002/anie.196706661 thesis.library.caltech.edu/656/1/Silver_ms_1959.pdf <BR> thesis.library.caltech.edu/4757/1/Cox_ef_1955.pdf The original literature arises from these two theses. $\endgroup$
    – Uncle Al
    Mar 29, 2014 at 19:13
  • $\begingroup$ Did you mean a 3-methyl cyclopropene carbocation? I believe that's the aromatic compound that is exceptionally stable (read: still not that stable) - a regular methyl cyclopropane would be very strained, and with a charge I think it would be even less so. $\endgroup$
    – qwersjc
    Mar 30, 2014 at 3:15
  • $\begingroup$ @qwersjc No I am not talking about that. $\endgroup$
    – evil999man
    Mar 30, 2014 at 10:12

1 Answer 1


George Olah and coworkers have examined the cyclobutyldicyclopropylmethyl and the cyclobutylmethyl cation.

(Yes, this is an awfully short answer and I can't really provide more information on the topic.)

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    $\begingroup$ Doesn't that require to buy the content? $\endgroup$
    – evil999man
    Mar 30, 2014 at 10:13
  • $\begingroup$ @Awesome Yes, unless you have access via a university or research facility. $\endgroup$ Mar 30, 2014 at 10:58
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    $\begingroup$ I don't have access. Could you just tell whether it will go rearrangement breaking ring or not? $\endgroup$
    – evil999man
    Mar 30, 2014 at 11:55

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