13
$\begingroup$

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?

$\endgroup$
3
  • 1
    $\begingroup$ 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

1
$\begingroup$

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.)

$\endgroup$
3
  • 2
    $\begingroup$ 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
  • 5
    $\begingroup$ 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

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.